Robert Burns Woodward: Difference between revisions

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{{short description|American chemist (1917–1979)}}

{{about|the Nobel Prize-winning chemist|the journalist|Bob Woodward}}

{{Other people|Robert Woodward}}

{{Use American English|date=June 2024}}

{{Infobox_Scientist

{{Use mdy dates|date=June 2024}}

| name = Robert Burns Woodward

{{Infobox scientist

| image =

| image_widthname = Robert Burns Woodward

| captionimage = Robert Woodward = Nobel.jpg

| birth_date = [[April{{birth date|1917|4|10]], [[1917]]|mf=y}}

| birth_name =

| birth_place = [[Boston]], [[Massachusetts]], [[USA]]

| death_date birth_place = [[July 8Boston]], [[1979]]Massachusetts, U.S.

| death_date = {{death date and age|1979|7|8|1917|4|10}}

| death_place = [[Cambridge, Massachusetts|Cambridge]], [[Massachusetts]], [[USA]]

| death_place = [[Cambridge, Massachusetts]], U.S.

| residence = {{flagcountry|USA}}

| citizenshipfield = {{flagcountry|USA}}[[Organic chemistry]]

| work_institution = [[Harvard University]]

| nationality =

| field alma_mater = [[Massachusetts Institute of Technology]] ([[B. =S.|BS]], [[Organic chemistryPhD]])

| doctoral_advisor = [[James Flack Norris]]<br>[[Avery Adrian Morton]]<ref>{{cite thesis|url=https://dspace.mit.edu/handle/1721.1/12465|title=A synthetic attack on the oestrone problem|publisher=MIT|year=1937|author=Woodward, Robert Burns|hdl=1721.1/12465 |type=Thesis }}</ref>

| work_institution = [[Harvard University]]

| thesis_title = A Synthetic Attack on the Oestrone Problem

| alma_mater = [[Massachusetts Institute of Technology|MIT]]

| doctoral_advisor thesis_year = 1937

| thesis_url = http://www.worldcat.org/oclc/29886711

| doctoral_students =

| doctoral_students = * [[Christopher Spencer Foote|Christopher Foote]]

| known_for = Quinine total synthesis, Strychnine total synthesis, Structure of Ferrocene, [[Woodward-Hoffmann rules]],

* [[Ken Houk]]

| prizes = [[National Medal of Science]] (1964)<br/>[[Image:Nobel.svg|20px]] [[Nobel Prize in Chemistry]] (1965)

* [[Ronald Breslow]]

* [[Stuart Schreiber]]

* [[William R. Roush]]

* [[David M. Lemal]]

| known_for = {{Plainlist|

* Landmark [[Organic synthesis|organic syntheses]]

* [[Molecular structure]] determination

* [[Vitamin B12 total synthesis]]

* [[Woodward cis-hydroxylation]]

* [[Oppenauer_oxidation#Woodward_modification|Woodward modification]]

* [[Strychnine_total_synthesis#Woodward_synthesis|Woodward synthesis]]

* [[Woodward's rules]]

* [[Quinine_total_synthesis#Woodward–Doering_formal_quinine_total_synthesis|Woodward–Doering quinine synthesis]]

* [[Woodward–Hoffmann rules]]

* [[Dihydroxylation#Prévost_and_Woodward_dihydroxylation|Prévost–Woodward reaction]]}}

| prizes = {{Plainlist|

* [[Centenary Prize]] {{small|(1951)}}

* [[Fellow of the Royal Society|ForMemRS]] {{small|(1956)}}<ref name=formemrs/>

* [[William H. Nichols Medal]] {{small|(1956)}}

* [[Davy Medal]] {{small|(1959)}}

* [[National Medal of Science]] <small>(1964)</small>

* [[Nobel Prize in Chemistry]] <small>(1965)</small>

* [[Willard Gibbs Award]] <small> (1967)</small>

* [[Copley Medal]] <small>(1978)</small>}}

}}

'''Robert Burns Woodward''' ([[April 10]], [[1917]]&ndash;[[July 8]], [[1979]]) was an [[United States|American]] [[organic chemistry|organic chemist]]. He made many important contributions to modern organic chemistry, especially in the synthesis and structure determination of complex natural products, and worked closely with [[Roald Hoffmann]] on theoretical studies of chemical reactions. Woodward won the [[Nobel Prize in Chemistry]] in 1965.

== Early life and education ==

Woodward was born in [[Boston, Massachusetts]], the son of Arthur Woodward (an immigrant from [[England]]) and Margaret Woodward, ''nee'' Burns (an immigrant from [[Scotland]], born in [[Glasgow]]).

'''Robert Burns Woodward''' {{postnominals|country=GBR|ForMemRS|HFRSE}} (April 10, 1917 – July 8, 1979) was an American [[Organic chemistry|organic chemist]]. He is considered by many to be the preeminent synthetic organic chemist of the twentieth century,<ref name=":1" /> having made many key contributions to the subject, especially in [[Organic synthesis|the synthesis of complex natural products]] and the determination of their [[molecular structure]]. He worked closely with [[Roald Hoffmann]] on theoretical studies of [[chemical reaction]]s. He was awarded the [[Nobel Prize in Chemistry]] in 1965.

From a very early age, Woodward was attracted to [[chemistry]] and engaged in private study while he attended the public primary and secondary schools of [[Quincy, Massachusetts]]. By the time he entered high school, he had already managed to perform most of the experiments in Paul Gatterman's then widely used textbook of experimental organic chemistry. In 1928, Woodward contacted the Consul-General of the German consulate in Boston, and through him, managed to obtain copies of a few original papers published in German journals. Later, in his Cope lecture, he recalled how he had been fascinated when, among these papers, he chanced upon Diels and Alder's original communication about the Diels-Alder reaction. Throughout his career, Woodward was to repeatedly and powerfully use and investigate this reaction, both in theoretical and experimental ways. In 1933, he entered the [[Massachusetts Institute of Technology]] (MIT), but neglected his formal studies badly enough to be expelled the next year. MIT readmitted him in 1935, and by 1936 he had received the [[Bachelor of Science]] degree. Only one year later, MIT awarded him the [[Doctor of Philosophy|doctorate]], when his classmates were still graduating with their bachelor's degrees. Woodward's doctoral work involved investigations related to the synthesis of the female sex hormone [[estrone]]. After a short postdoctoral stint at the University of Illinois, he took a Junior Fellowship at [[Harvard University]] from 1937 to 1938, and remained at Harvard in various capacities for the rest of his life. In the 1960s, Woodward was named Donner Professor of Science, a title that freed him from teaching formal courses so that he could devote his entire time to research.

== Early worklife and education==

Woodward was born in [[Boston, Massachusetts]], on April 10, 1917. He was the son of Margaret Burns (an immigrant from Scotland who claimed to be a descendant of the poet, [[Robert Burns]]) and her husband, Arthur Chester Woodward, himself the son of [[Roxbury, Boston|Roxbury]] apothecary, Harlow Elliot Woodward.

The first major contribution of Woodward's career in the early 1940s was a series of papers describing the application of [[ultraviolet]] [[spectroscopy]] in the elucidation of the structure of natural products. Woodward collected together a large amount of empirical data, and then devised a series of rules later called the Woodward rules, which could be applied to finding out the structures of new natural substances, as well as non-natural synthesized molecules. The expedient use of newly developed instrumental techniques was a characteristic Woodward exemplified throughout his career, and it marked a radical change from the extremely tedious and long chemical methods of structural elucidation that had been used until then.

His father was one of the many victims of the [[1918 influenza pandemic]].

In 1944, with his post doctoral researcher, William von Doering, Woodward reported the synthesis of the [[alkaloid]] [[quinine]], used to treat [[malaria]]. Although the synthesis was publicized as a breakthrough in procuring the hard to get medicinal compound from Japanese occupied southeast Asia, in reality it was too long and tedious to adopt on a practical scale. Nevertheless it was a landmark for chemical synthesis. Woodward's particular insight in this synthesis was to realise that the German chemist Paul Rabe had converted a precursor of quinine called quinotoxine to quinine in 1905. Hence, a synthesis of quinotoxine (which Woodward actually synthesized)) would establish a route to synthesizing quinine. When Woodward accomplished this feat, organic synthesis was still largely a matter of trial and error, and nobody thought that such complex structures could actually be constructed. Woodward showed that organic synthesis could be made into a rational science, and that synthesis could be aided by well-established principles of reactivity and structure. This synthesis was the first one in a series of exceedingly complicated and elegant syntheses that he would undertake.

From a very early age, Woodward was attracted to and engaged in private study of [[chemistry]] while he attended a public primary school, and then [[Quincy High School (Massachusetts)|Quincy High School]],<ref>{{cite book | last =Putnam | first =Robert C. | year = 2001 | editor1-last = Benfey | editor1-first = Otto Theodor | editor2-last = Turnbull Morris | editor2-first = Peter John | title = Reminiscences From Junior High School | work =Robert Burns Woodward: Architect and Artist in the World of Molecules | url =https://books.google.com/books?id=jMoiQSZUktoC&pg=PP1 | publisher =Chemical Heritage Foundation | page =12| isbn =9780941901253 }}</ref> in [[Quincy, Massachusetts]]. By the time he entered high school, he had already managed to perform most of the experiments in [[Ludwig Gattermann]]'s then widely used textbook of experimental organic chemistry. In 1928, Woodward contacted the Consul-General of the German consulate in Boston (Baron von Tippelskirch <ref name=halford />), and through him, managed to obtain copies of a few original papers published in German journals. Later, in his Cope lecture, he recalled how he had been fascinated when, among these papers, he chanced upon Diels and Alder's original communication about the [[Diels–Alder reaction]]. Throughout his career, Woodward was to repeatedly and powerfully use and investigate this reaction, both in theoretical and experimental ways. In 1933, he entered the [[Massachusetts Institute of Technology]] (MIT), but neglected his formal studies badly enough to be excluded at the end of the 1934 fall term. MIT readmitted him in the 1935 fall term, and by 1936 he had received the [[Bachelor of Science]] degree. Only one year later, MIT awarded him the [[Doctor of Philosophy|doctorate]], when his classmates were still graduating with their bachelor's degrees.<ref name=":0">[https://www.nobelprize.org/nobel_prizes/chemistry/laureates/1965/woodward-bio.html The Nobel Prize in Chemistry 1965 – Robert B. Woodward Biography] Nobelprize.org</ref> Woodward's doctoral work involved investigations related to the synthesis of the female sex hormone [[estrone]].<ref>[http://dspace.mit.edu/handle/1721.1/12465 A synthetic attack on the oestrone problem PhD dissertation]</ref> MIT required that graduate students have research advisors. Woodward's advisors were [[James Flack Norris]] and Avery Adrian Morton,{{citation needed|date=August 2017}} although it is not clear whether he actually took any of their advice. After a short postdoctoral stint at the University of Illinois, he took a Junior Fellowship at [[Harvard University]] from 1937 to 1938, and remained at Harvard in various capacities for the rest of his life. In the 1960s, Woodward was named Donner Professor of Science, a title that freed him from teaching formal courses so that he could devote his entire time to research.

== Later work and its impact ==

Culminating in the 1930s, the British chemists [[Christopher Ingold]] and [[Robert Robinson (scientist)|Robert Robinson]] among others had investigated the mechanisms of organic reactions, and had come up with empirical rules which could predict reactivity of organic molecules. Woodward was perhaps the first synthetic organic chemist who used these ideas as a predictive framework in synthesis. Woodward's style was the inspiration for the work of hundreds of successive synthetic chemists who synthesized medicinally important and structurally complex natural products.

=== Organic synthesesResearch and Nobel Prize =career==

During the late 1940s, Woodward synthesized many complex natural products including [[quinine]], [[cholesterol]], [[cortisone]], [[strychnine]], [[lysergic acid]], [[reserpine]], [[chlorophyll]], [[cephalosporin]], and [[colchicine]]. With these, Woodward opened up a new era of synthesis, sometimes called the 'Woodwardian era' in which he showed that natural products could be synthesized by careful applications of the principles of physical organic chemistry, and by meticulous planning.

===Early work===

Many of Woodward's syntheses were described as spectacular by his colleagues and before he did them, it was thought by some that it would be impossible to create these substances in the lab. Woodward's syntheses were also described as having an element of art in them, and since then, synthetic chemists have always looked for elegance as well as utility in synthesis. His work also involved the exhaustive use of the then newly developed techniques of [[infrared spectroscopy]] and later, [[nuclear magnetic resonance]] [[spectroscopy]]. Another important feature of Woodward's syntheses was their attention to [[stereochemistry]] or the particular configuration of molecules in three dimensional space. Most natural products of medicinal importance are effective, for example as drugs, only when they possess a specific stereochemistry. This creates the demand for 'stereospecific synthesis', producing a compound with a defined stereochemistry. While today a typical synthetic route routinely involves such a procedure, Woodward was a pioneer in showing how, with exhaustive and rational planning, one could conduct reactions that were stereospecific. Many of his syntheses involved forcing a molecule into a certain configuration by installing rigid structural elements in it, another tactic that has become standard today. In this regard, especially his syntheses of [[reserpine]] and [[strychnine]] were landmarks.

The first major contribution of Woodward's career in the early 1940s was a series of papers describing the application of [[ultraviolet]] [[spectroscopy]] in the elucidation of the structure of natural products. Woodward collected together a large amount of empirical data, and then devised a series of rules later called the [[Woodward's rules]], which could be applied to finding out the structures of new natural substances, as well as non-natural synthesized molecules. The expedient use of newly developed instrumental techniques was a characteristic Woodward exemplified throughout his career, and it marked a radical change from the extremely tedious and long chemical methods of structural elucidation that had been used until then.

In 1944, with his post doctoral researcher, [[William von Eggers Doering]], Woodward reported the synthesis of the [[alkaloid]] [[quinine]], used to treat [[malaria]]. Although the synthesis was publicized as a breakthrough in procuring the hard to get medicinal compound from Japanese occupied southeast Asia, in reality it was too long and tedious to adopt on a practical scale. Nevertheless, it was a landmark for chemical synthesis. Woodward's particular insight in this synthesis was to realize that the German chemist Paul Rabe had converted a precursor of quinine called quinotoxine to quinine in 1905. Hence, a synthesis of quinotoxine (which Woodward actually synthesized) would establish a route to synthesizing quinine. When Woodward accomplished this feat, organic synthesis was still largely a matter of trial and error, and nobody thought that such complex structures could actually be constructed. Woodward showed that organic synthesis could be made into a rational science, and that synthesis could be aided by well-established principles of reactivity and structure. This synthesis was the first one in a series of exceedingly complicated and elegant syntheses that he would undertake.

Woodward also applied the technique of [[infrared spectroscopy]] and chemical degradation to determine the structures of complicated molecules. Notable among these structure determinations were santonic acid, [[strychnine]], [[magnamycin]] and [[terramycin]]. During the war years, Woodward also proposed the correct structure of [[penicillin]] as a beta-[[lactam]], as opposed to the [[thiazolidine]]-[[oxazolone]] structure proposed by [[Robert Robinson (scientist)|Robert Robinson]], the then leading organic chemist of his generation. About terramycin, Woodward's colleague and Nobel Laureate [[Derek Barton]] said:

:''The most brilliant analysis ever done on a structural puzzle was surely the solution (1953) of the terramycin problem. It was a problem of great industrial importance, and hence many able chemists had performed an enormous amount of work trying to determine the structure. There seemed to be too much data to resolve the problem, because a significant number of observations, although experimentally correct, were very misleading. Woodward took a large piece of cardboard, wrote on it all the facts and, by thought alone, deduced the correct structure for terramycin. Nobody else could have done that at the time.''

In each one of these cases, Woodward again showed how rational facts and chemical principles, combined with chemical intuition, could be used to achieve the task.

===Later work and its impact===

In the early 1950s, Woodward, along with the British chemist [[Geoffrey Wilkinson]], then at Harvard, postulated a novel structure for [[ferrocene]], a compound consisting of a combination of an organic molecule with iron. This marked the beginning of the field of [[organometallic chemistry]] which grew into an industrially very significant field. Wilkinson won the Nobel Prize for this work in 1973, along with [[Ernst Otto Fischer]]. Some historians think that Woodward should have shared this prize along with Wilkinson. Remarkably, Woodward himself thought so, and voiced his thoughts in a letter sent to the Nobel Committee.

[[File:Robert Burns Woodward in 1965.jpg|thumb|Woodward talked about [[Chlorophyll]] in 1965]]

Culminating in the 1930s, the British chemists [[Christopher Ingold]] and [[Robert Robinson (organic chemist)|Robert Robinson]] among others had investigated the mechanisms of organic reactions, and had come up with empirical rules which could predict reactivity of organic molecules. Woodward was perhaps the first synthetic organic chemist who used these ideas as a predictive framework in synthesis. Woodward's style was the inspiration for the work of hundreds of successive synthetic chemists who synthesized medicinally important and structurally complex natural products.

===Organic syntheses and Nobel Prize===

Woodward won the Nobel Prize in 1965 for his synthesis of complex organic molecules. In his Nobel lecture, he described the total synthesis of the antibiotic [[cephalosporin]], and claimed that he had pushed the synthesis schedule so that it would be completed around the time of the Nobel ceremony.

{{more citations needed section|date=June 2024}}

During the late 1940s, Woodward synthesized many complex natural products including [[quinine]], [[cholesterol]], [[cortisone]], [[strychnine]], [[lysergic acid]], [[reserpine]], [[chlorophyll]], [[cephalosporin]], and [[colchicine]].<ref>{{cite web|url=https://www.nytimes.com/1960/07/03/archives/science-notes-chlorophyll.html |title= Chlorophyll |quote=Prof. Robert Burns Woodward, the Harvard chemist who synthesized quinine, cortisone and rauwolfia, has now achieved one of the greatest triumphs in chemistry – the total synthesis of chlorophyll, the green pigment that captures the energy of sunlight for the creation of the food for all things living. ...|work=[[The New York Times]]|date=July 3, 1960 |access-date=October 13, 2012}}</ref> With these, Woodward opened up a new era of synthesis, sometimes called the 'Woodwardian era' in which he showed that natural products could be synthesized by careful applications of the principles of [[physical organic chemistry]], and by meticulous planning.

Many of Woodward's syntheses were described as spectacular by his colleagues and before he did them, it was thought by some that it would be impossible to create these substances in the lab. Woodward's syntheses were also described as having an element of art in them, and since then, synthetic chemists have always looked for elegance as well as utility in synthesis. His work also involved the exhaustive use of the then newly developed techniques of [[infrared spectroscopy]] and later, [[nuclear magnetic resonance]] [[spectroscopy]]. Another important feature of Woodward's syntheses was their attention to [[stereochemistry]] or the particular configuration of molecules in three-dimensional space. Most natural products of medicinal importance are effective, for example as drugs, only when they possess a specific stereochemistry. This creates the demand for '[[Enantioselective synthesis|stereoselective synthesis]]', producing a compound with a defined stereochemistry. While today a typical synthetic route routinely involves such a procedure, Woodward was a pioneer in showing how, with exhaustive and rational planning, one could conduct reactions that were stereoselective. Many of his syntheses involved forcing a molecule into a certain configuration by installing rigid structural elements in it, another tactic that has become standard today. In this regard, especially his syntheses of reserpine and strychnine were landmarks.

=== B12 synthesis and Woodward-Hoffmann rules ===

In the early 1960s, Woodward began work on what was the most complex natural product synthesized to date- Vitamin B12. In a remarkable collaboration with his colleague [[Albert Eschenmoser]] in Zurich, a team of almost one hundred students and postdoctoral workers worked for many years on the synthesis of this molecule. The work was finally published in 1973, and it marked a landmark in the history of organic chemistry. The synthesis included almost a hundred steps, and involved the characteristic rigorous planning and analyses that had always characterised Woodward's work. This work, more than any other, convinced organic chemists that the synthesis of any complex substance was possible, given enough time and planning. However, as of 2006, no other total synthesis of Vitamin B12 has been published.

During World War II, Woodward was an advisor to the [[War Production Board]] on the penicillin project. Although often given credit for proposing the [[beta-lactam]] structure of [[penicillin]], it was actually first proposed by chemists at [[Merck & Co.|Merck]] and [[Edward Abraham]] at Oxford and then investigated by other groups, as well (e.g., Shell). Woodward at first endorsed an incorrect tricyclic ([[thiazolidine]] fused, amino bridged oxazinone) structure put forth by the penicillin group at Peoria. Subsequently, he put his [[imprimatur]] on the beta-lactam structure, all of this in opposition to the [[thiazolidine]]&ndash;[[oxazolone]] structure proposed by [[Robert Robinson (organic chemist)|Robert Robinson]], the then leading organic chemist of his generation. Ultimately, the beta-lactam structure was shown to be correct by [[Dorothy Hodgkin]] using [[X-ray crystallography]] in 1945.

That same year, based on observations that Woodward had made during the B12 synthesis, he and [[Roald Hoffmann]] devised rules (now called the [[Woodward-Hoffmann rules]]) for elucidating the [[stereochemistry]] of the products of [[organic chemistry|organic]] [[chemical reaction|reactions]]. Woodward formulated his ideas (which were based on the [[symmetry]] properties of [[molecular orbital]]s) based on his experiences as a synthetic organic chemist; he asked Hoffman to perform theoretical calculations to verify these ideas, which were done using Hoffmann's [[Extended Huckel method|Extended Hückel method]]. The predictions of these rules, called the "Woodward-Hoffmann rules" were verified by many experiments. Hoffmann shared the 1981 Nobel Prize for this work along with [[Kenichi Fukui]], a Japanese chemist who had done similar work using a different approach; Woodward undoubtedly would have received a second Nobel Prize as well had he lived.

Woodward also applied the technique of [[infrared spectroscopy]] and chemical degradation to determine the structures of complicated molecules. Notable among these structure determinations were [[santonic acid]], strychnine, [[magnamycin]] and [[terramycin]]. In each one of these cases, Woodward again showed how rational facts and chemical principles, combined with chemical intuition, could be used to achieve the task.

=== Woodward Institute and later life ===

While still remaining at Harvard, Woodward took on the directorship of the [[Woodward Research Institute]], based at [[Basel]], Switzerland in 1963. He also became a trustee of his alma mater, MIT, from 1966 to 1971 and of the [[Weizmann Institute of Science]] in [[Israel]].

In the early 1950s, Woodward, along with the British chemist [[Geoffrey Wilkinson]], then at Harvard, postulated a novel structure for [[ferrocene]], a compound consisting of a combination of an organic molecule with iron.<ref>{{Cite journal|last1 = Wilkinson|first1 = G.|author-link1 = Geoffrey Wilkinson|last2 = Rosenblum|first2 = M.|last3 = Whiting|first3 = M. C.|last4 = Woodward|first4 = R. B.|author-link4 = Robert Burns Woodward|title = The Structure of Iron ''Bis''-Cyclopentadienyl|journal = [[J. Am. Chem. Soc.]]|year = 1952|volume = 74|issue = 8|pages = 2125–2126|doi = 10.1021/ja01128a527| bibcode=1952JAChS..74.2125W }}</ref> This marked the beginning of the field of [[transition metal]] [[organometallic chemistry]] which grew into an industrially very significant field.<ref>{{Cite journal|doi = 10.1002/chin.200443242|title = Ferrocene: 50 Years of Transition Metal Organometallic Chemistry — From Organic and Inorganic to Supramolecular Chemistry|year = 2004|last1 = Federman Neto|first1 = A.|last2 = Pelegrino|first2 = A. C.|last3 = Darin|first3 = V. A.|journal = ChemInform|volume = 35|issue = 43 | article-number=chin.200443242 }}</ref> Wilkinson won the Nobel Prize for this work in 1973, along with [[Ernst Otto Fischer]].<ref>{{Cite web|url= http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/|title= The Nobel Prize in Chemistry 1973|publisher= [[Nobel Prize|nobelprize.org]]|access-date= September 12, 2010}}</ref> Some historians think that Woodward should have shared this prize along with Wilkinson. Remarkably, Woodward himself thought so, and voiced his thoughts in a letter sent to the Nobel Committee.<ref>{{cite book|title = Landmarks in Organo-Transition Metal Chemistry: A Personal View|author = Werner, H.|year = 2008|publisher = Springer Science|pages = 161–163|isbn = 978-0-387-09847-0|url = https://books.google.com/books?id=dP4LTfaPzAMC&pg=PA161}}</ref>

Woodward died in [[Cambridge, Massachusetts]] from a [[myocardial infarction|heart attack]] in his sleep. At the time, he was working on the synthesis of an [[antibiotic]], [[erythromycin]]. A student of his said about him:

:''I owe a lot to R. B. Woodward. He showed me that one could attack difficult problems without a clear idea of their outcome, but with confidence that intelligence and effort would solve them. He showed me the beauty of modern organic chemistry, and the relevance to the field of detailed careful reasoning. He showed me that one does not need to specialize. Woodward made great contributions to the strategy of synthesis, to the deduction of difficult structures, to the invention of new chemistry, and to theoretical aspects as well. He taught his students by example the satisfaction that comes from total immersion in our science. I treasure the memory of my association with this remarkable chemist.''

Woodward won the Nobel Prize in 1965 for his synthesis of complex organic molecules. He had been nominated a total of 111 times from 1946 to 1965.<ref>{{Cite web | url=https://www.nobelprize.org/nomination/archive/show_people.php?id=10302 |title = Nomination Archive| date=April 2020 }}</ref> In his Nobel lecture, he described the total synthesis of the antibiotic cephalosporin, and claimed that he had pushed the synthesis schedule so that it would be completed around the time of the Nobel ceremony.

Many regard Woodward to be the pre-eminent organic chemist of the latter half of the twentieth century.

===B₁₂ synthesis and Woodward–Hoffmann rules===

== Other notes ==

In the early 1960s, Woodward began work on what was the most complex natural product synthesized to date—[[Vitamin B12|vitamin B₁₂]]. In a remarkable collaboration with his colleague [[Albert Eschenmoser]] in Zurich, a team of almost one hundred students and postdoctoral workers worked for many years on the synthesis of this molecule. The work was finally published in 1973, and it marked a landmark in the history of organic chemistry. The synthesis included almost a hundred steps, and involved the characteristic rigorous planning and analyses that had always characterised Woodward's work. This work, more than any other, convinced organic chemists that the synthesis of any complex substance was possible, given enough time and planning (see also [[Palytoxin#Total synthesis|palytoxin]], synthesized by the research group of [[Yoshito Kishi]], one of Woodward's postdoctoral students). As of 2019, no other [[Vitamin B12 total synthesis|total synthesis of Vitamin B₁₂]] has been published.

In 1938 he married Irja Pullman, and in 1946 he married Eudoxia Muller. From the first marriage he had two daughters, and from the second one daughter and one son.

That same year, based on observations that Woodward had made during the B₁₂ synthesis, he and [[Roald Hoffmann]] devised rules (now called the [[Woodward–Hoffmann rules]]) for elucidating the [[stereochemistry]] of the products of [[organic chemistry|organic]] [[chemical reaction|reactions]].<ref>{{Cite journal

During his lifetime Woodward authored or coauthored 196 publications, of which 85 are full papers, the remainder comprising preliminary communications, the text of lectures, and reviews. The pace of his scientific activity soon outstripped his capacity to publish all experimental details, and much of the work he participated was published even till a few years after his death. Woodward trained more than two hundred talented PhD. students and postdoctoral workers, many of who later went on to distinguished careers. Some of his best-known students include [[Yoshito Kishi]] (Harvard), [[Stuart Schreiber]] (Harvard), [[Steven A. Benner]] (UF), [[Christopher S. Foote]] (UCLA), [[Kendall Houk]] (UCLA), and porphyrin chemist Kevin M. Smith. Smith was recently awarded the Robert Burns Woodward Award for Lifetime Achievement at the International Conference on Porphyrins and Pthalocyanines (ICPP- 4) held at Rome.

|pmid=17742608

|last1=Hoffmann

|first1=R.

|author-link1=Roald Hoffmann

|last2=Woodward

|first2=R. B.

|author-link2=Robert Burns Woodward

|publication-date=February 6, 1970

|year=1970

|title=Orbital Symmetry Control of Chemical Reactions

|volume=167

|issue=3919

|journal=[[Science (journal)|Science]]

|pages=825–831

|doi = 10.1126/science.167.3919.825

|bibcode = 1970Sci...167..825H |s2cid=12243669

}}</ref> Woodward formulated his ideas (which were based on the [[symmetry]] properties of [[molecular orbital]]s) based on his experiences as a synthetic organic chemist; he asked Hoffman to perform theoretical calculations to verify these ideas, which were done using Hoffmann's [[Extended Hückel method]]. The predictions of these rules, called the "[[Woodward–Hoffmann rules]]" were verified by many experiments. Hoffmann shared the 1981 Nobel Prize for this work along with [[Kenichi Fukui]], a Japanese chemist who had done similar work using a different approach; Woodward had died in 1979 and Nobel Prizes are not awarded posthumously.

===Woodward Institute===

Woodward was known to be a workaholic and devoted almost all his time to chemistry. He had an encyclopaedic knowledge of chemistry, and an extraordinary memory for detail. Probably the quality that most set him apart from his peers was his remarkable ability to tie together disparate threads of knowledge from the chemical literature and bring them to bear on a chemical problem. His lectures were legendary and frequently used to last for three or four hours. In many of these, he eschewed the use of slides and used to draw beautiful structures by using coloured chalk. His famous Thursday seminars at Harvard also used to frequently last well into the night. He had a fixation with blue, and all his suits, his car, and even his parking space were coloured in blue. He detested exercise, could get along with only a few hours of sleep every night, was a [[chain smoking|heavy smoker]] [http://www.chemistry.msu.edu/Portraits/PortraitsHH_Detail.asp?HH_Lname=WoodwardB], and enjoyed Scotch whisky and a martini or two.

While at Harvard, Woodward took on the directorship of the

'''Woodward Research Institute''', based at [[Basel]], Switzerland, in 1963.<ref name=Craig>{{cite journal|doi=10.1002/hlca.201100077|title=The Woodward Research Institute, Robert Burns Woodward (1917–1979) and Chemistry behind the Glass Door|year=2011|last1=Craig|first1=G. Wayne|journal=Helvetica Chimica Acta|volume=94|issue=6|pages=923–946 |bibcode=2011HChAc..94..923C }}</ref> He also became a trustee of his alma mater, [[Massachusetts Institute of Technology|MIT]], from 1966 to 1971, and of the [[Weizmann Institute of Science]] in Israel.{{citation needed|date=June 2024}}

===Death===

== Honors and awards ==

{{Unreferenced section|date=June 2024}}

For his work, Woodward received many awards, honors and honorary doctorates, including election to the National Academy of Sciences in 1953, and membership in academies around the world. He was also a consultant to many companies such as Polaroid, [[Pfizer]], and [[Merck]]. Other awards include:

Woodward died in [[Cambridge, Massachusetts]], from a [[myocardial infarction|heart attack]] in his sleep. At the time, he was working on the synthesis of an [[antibiotic]], [[erythromycin]]. A student of his said about him:{{cite needed|date=December 2022}}

:''I owe a lot to R. B. Woodward. He showed me that one could attack difficult problems without a clear idea of their outcome, but with confidence that intelligence and effort would solve them. He showed me the beauty of modern organic chemistry, and the relevance to the field of detailed careful reasoning. He showed me that one does not need to specialize. Woodward made great contributions to the strategy of synthesis, to the deduction of difficult structures, to the invention of new chemistry, and to theoretical aspects as well. He taught his students by example the satisfaction that comes from total immersion in our science. I treasure the memory of my association with this remarkable chemist.''

* [[John Scott]] Medal, from the [[Franklin Institute]] and City of [[Philadelphia]], 1945

* [[Backeland]] Medal, from the North Jersey Section of the [[American Chemical Society]], 1955

===Publications===

* [[Humphry Davy|Davy]] Medal, from the [[Royal Society]] in 1959

During his lifetime Woodward authored or coauthored almost 200 publications, of which 85 are full papers, the remainder comprising preliminary communications, the text of lectures, and reviews. The pace of his scientific activity soon outstripped his capacity to publish all experimental details, and much of the work in which he participated was not published until a few years after his death. Woodward trained more than two hundred Ph.D. students and postdoctoral workers, many of whom later went on to distinguished careers.

* [[Roger Adams]] Medal, from the American Chemical Society in 1961

* [[Pius XI]] Gold Medal, from the Pontifical Academy of Sciences in 1969

Some of his best-known students include [https://web.archive.org/web/20100718223149/http://rwindigo1.chm.colostate.edu/ Robert M. Williams] (Colorado State), Harry Wasserman (Yale), [[Yoshito Kishi]] (Harvard), [[Stuart Schreiber]] (Harvard), [[William R. Roush]] ([[Scripps Research Institute|Scripps-Florida]]), [[Steven Albert Benner|Steven A. Benner]] (UF), [[James D. Wuest]] (Montreal), [[Christopher S. Foote]] (UCLA), [[Kendall Houk]] (UCLA), porphyrin chemist Kevin M. Smith (LSU), Thomas R. Hoye (University of Minnesota), [[Ronald Breslow]] (Columbia University) and [[David Dolphin]] (UBC).

* [[National Medal of Science]] from the [[United States|United States of America]] in 1964 ("''For an imaginative new approach to the synthesis of complex organic molecules and, especially, for [his] brilliant syntheses of strychnine, reserphine, lysergic acid, and chlorophyll.''")

Woodward had an encyclopedic knowledge of chemistry, and an extraordinary memory for detail.<ref name="Roberts, J. 1990">{{cite book|title = The Right Place at the Right Time|author = Roberts, J.|year = 1990|publisher = [[American Chemical Society]]|isbn = 978-0-8412-1766-9}}</ref> Probably the quality that most set him apart from his peers was his remarkable ability to tie together disparate threads of knowledge from the chemical literature and bring them to bear on a chemical problem.<ref name="Roberts, J. 1990"/>

==Honors and awards==

For his work, Woodward received many awards, honors and honorary doctorates, including election to the [[American Academy of Arts and Sciences]] in 1948,<ref>{{Cite web |title=Robert Burns Woodward |url=https://www.amacad.org/person/robert-burns-woodward |access-date=November 14, 2022 |website=American Academy of Arts & Sciences |language=en}}</ref> the [[National Academy of Sciences]] in 1953,<ref>{{Cite web |title=Robert Woodward |url=http://www.nasonline.org/member-directory/deceased-members/20000740.html |access-date=November 14, 2022 |website=www.nasonline.org}}</ref> the [[American Philosophical Society]] in 1962,<ref>{{Cite web |title=APS Member History |url=https://search.amphilsoc.org/memhist/search?creator=Robert+B.+Woodward&title=&subject=&subdiv=&mem=&year=&year-max=&dead=&keyword=&smode=advanced |access-date=November 14, 2022 |website=search.amphilsoc.org}}</ref> and membership in academies around the world. He was also a consultant to many companies such as Polaroid, [[Pfizer]], and [[Merck & Co.|Merck]]. Other awards include:

{{div col|colwidth=35em}}

* [[John Scott Medal]], from the [[Franklin Institute]] and City of [[Philadelphia]], 1945

* [[Leo Hendrik Baekeland Award]], from the North Jersey Section of the [[American Chemical Society]], 1955<ref>[http://www.njacs.org/awards Awards] North Jersey Section American Chemical Society – see section Current & Past Recipients of the Leo Hendrik Baekeland Award</ref>

* Elected a [[List of Fellows of the Royal Society elected in 1956|Foreign Member of the Royal Society (ForMemRS) in 1956]]<ref name=formemrs/>

* [[Davy Medal]], from the [[Royal Society]] in 1959

* Roger Adams Medal, from the American Chemical Society in 1961{{citation needed|date=March 2016}}

* Pius XI Gold Medal, from the Pontifical Academy of Sciences in 1969{{citation needed|date=March 2016}}

* [[National Medal of Science]] from the United States in 1964 ("''For an imaginative new approach to the synthesis of complex organic molecules and, especially, for his brilliant syntheses of strychnine, reserphine, lysergic acid, and chlorophyll.''")

* [[Nobel Prize in Chemistry]] in 1965

* [[Willard Gibbs Award]] Medal from the [[Chicago]] Section of the American Chemical Society in 1967<ref>[http://chicagoacs.org/content.php?page=Willard_Gibbs_Award American Chemical Society – Chicago Section]</ref>

* [[Lavoisier Medal]] Medal from the [[SocieteSociété Chimiquechimique de France]] in 1968

* The [[Order of the Rising Sun]], Second Class from the Emperor of [[Japan]] in 1970

* [[Hanbury Memorial Medal]] from The Pharmaceutical Society of [[Great Britain]] in 1970{{citation needed|date=March 2016}}

* [[Pierre Brnylants]]Bruylants Medal from the [[Université catholique de Louvain|University of Louvain]] in 1970{{citation needed|date=March 2016}}

* [[AMA Scientific Achievement Award]] in 1971

* [[Arthur C. Cope Award|Cope Award]] from the American Chemical Society, shared with [[Roald Hoffmann]] in 1973

* [[Copley Medal]] from the Royal Society, London in 1978

{{div col end}}

===Honorary degrees===

Woodward also received over twenty honorary degrees, including honorary doctorates from the following universities:

Woodward also received over twenty [[honorary degrees]],<ref name=":1">{{cite web |last1=Blout |first1=Elkan |title=Robert Burns Woodward 1917–1979: A Biographical Memoir |url=http://www.nasonline.org/publications/biographical-memoirs/memoir-pdfs/woodward-robert-b.pdf#page=4 |archive-url=https://web.archive.org/web/20170116171636/http://www.nasonline.org/publications/biographical-memoirs/memoir-pdfs/woodward-robert-b.pdf |archive-date=January 16, 2017 |access-date=January 15, 2017 |website=National Academy of Sciences |publisher=The National Academy Press}}</ref> including honorary doctorates from the following universities:

* [[Wesleyan University]] in 1945;

{{div col|colwidth=35em}}

* [[Harvard University]] in 1957;

* [[Wesleyan University of Cambridge]] in 19641945;

* [[BrandeisHarvard University]] in 19651957;

* [[University of Cambridge]] in 1964;{{citation needed|date=March 2016}}

* [[Technion Israel Institute of Technology]] in [[Haifa]] in 1966;

* [[Brandeis University of Western Ontario]] in [[Canada]] in 19681965;

* [[UniversityTechnion Israel Institute of LouvainTechnology]] in [[BelgiumHaifa]], 1970.in 1966;

* [[University of Western Ontario]] in Canada in 1968;

* [[Université catholique de Louvain|University of Louvain]] in Belgium, 1970.

{{div col end}}

==Personal life==

{{start box}}

{{np-chem-sb}}

{{succession box|title=[[Nobel Prize in Chemistry]]

| before=[[Dorothy Crowfoot Hodgkin]]

| after=[[Robert S. Mulliken]]

| years=1965

}}

{{end box}}

== References =Family===

In 1938, he married Irja Pullman; they had two daughters: Siiri Anna (b. 1939) and Jean Kirsten (b. 1944). In 1946, he married [[Eudoxia Woodward|Eudoxia Muller]], an artist and technician whom he met at [[Polaroid Corporation|the Polaroid Corp.]] This marriage, which lasted until 1972, produced a daughter, and a son: Crystal Elisabeth (b. 1947), and Eric Richard Arthur (b. 1953).<ref name=":0" />

# "Robert Burns Woodward" by Elkan Blout in 'Biographical Memoirs'; National Academy of Sciences Press, Vol. 80, 2001.

# Robert Burns Woodward: Architect and Artist in the World of Molecules; Otto Theodor Benfey, Peter J. T. Morris, Chemical Heritage Foundation, April 2001.

# Robert Burns Woodward and the Art of Organic Synthesis: To Accompany an Exhibit by the Beckman Center for the History of Chemistry (Publication / Beckman Center for the History of Chemistry); Mary E. Bowden; Chemical Heritage Foundation, March 1992

# "Robert Burns Woodward"- Biographical Memoirs of Fellows of the Royal Society: Alexander Todd and John Cornforth (Nov. 1981)

#{{cite journal

| author= Woodward R. B., Sondheimer F., Taub D.

| title= The Total Synthesis of Cortisone

| journal=Journal of the American Chemical Society

| year=1951

| pages=4057 - 4057

| volume=73

| doi=10.1021/ja01152a551 }}

===Idiosyncrasies===

== See also ==

His lectures frequently lasted for three or four hours.<ref name=halford>''Remembering organic chemistry legend Robert Burns Woodward Famed chemist would have been 100 this year'' By Bethany Halford C&EN Volume 95 Issue 15 | pp. 28–34 Issue Date: April 10, 2017 [http://cen.acs.org/articles/95/i15/Remembering-organic-chemistry-legend-Robert-Burns-Woodward.html link].</ref> His longest known lecture defined the unit of time known as the "Woodward", after which his other lectures were deemed to be so many "milli-Woodwards" long.<ref>{{in lang|fr}}[https://books.google.com/books?id=rxn5m7w_mgsC&dq=milli-Woodward&pg=PA115 Introduction à la chimie quantique] Philippe Hiberty and Nguyên Trong Anh, Editions Ecole Polytechnique

* [[Woodward cis-hydroxylation]]

Renaud-Bray (2008) p.115 {{ISBN|2730214852}}</ref> In many of these, he eschewed the use of slides and drew structures by using multicolored chalk. Typically, to begin a lecture, Woodward would arrive and lay out two large white handkerchiefs on the countertop. Upon one would be four or five colors of chalk (new pieces), neatly sorted by color, in a long row. Upon the other handkerchief would be placed an equally impressive row of cigarettes. The previous cigarette would be used to light the next one. His Thursday seminars at Harvard often lasted well into the night. He had a fixation with blue, and many of his suits, his car, and even his parking space were coloured in blue.<ref name=halford />

In one of his laboratories, his students hung a large black and white photograph of the master from the ceiling, complete with a large blue "tie" appended. There it hung for some years (early 1970s), until scorched in a minor laboratory fire.{{Citation needed|date=March 2012}} He detested exercise, could get along with only a few hours of sleep every night, was a [[chain smoking|heavy smoker]], and enjoyed Scotch whisky and martinis.<ref name="formemrs">{{cite journal|last1=Todd|first1=L.|last2=Cornforth|first2=J.|last3=T.|first3=A. R.|last4=C.|first4=J. W.|title=Robert Burns Woodward. 10 April 1917-8 July 1979|journal=Biographical Memoirs of Fellows of the Royal Society|volume=27|year=1981|pages=628–695|issn=0080-4606|doi=10.1098/rsbm.1981.0025|doi-access=|s2cid=71742454 }}</ref><ref>[http://www.chemistry.msu.edu/Portraits/PortraitsHH_Detail.asp?HH_Lname=WoodwardB Robert Burns Woodward] {{webarchive|url=https://web.archive.org/web/20120427012737/http://www2.chemistry.msu.edu/Portraits/PortraitsHH_Detail.asp?HH_Lname=WoodwardB |date=April 27, 2012 }}.</ref>

== External links ==

*[http://nobelprize.org/chemistry/laureates/1965/index.html Robert Burns Woodward]

*[http://www.ch.ic.ac.uk/video/index.rss Video podcast of Robert Burns Woodward talking about cephalosporin]

*[http://www.patentgenius.com/inventor/WoodwardRobertBurns.html Robert Burns Woodward Patents]

==References==

{{Nobel Prize in Chemistry}}

{{Reflist|35em}}

==Bibliography==

<!-- Metadata: see [[Wikipedia:Persondata]] -->

{{Expand-list|date=March 2022}}

{{Persondata

{{div col|colwidth=35em}}

|NAME=Woodward, Robert Burns

* Robert Burns Woodward: Architect and Artist in the World of Molecules; Otto Theodor Benfey, Peter J. T. Morris, Chemical Heritage Foundation, April 2001.

|ALTERNATIVE NAMES=

* Robert Burns Woodward and the Art of Organic Synthesis: To Accompany an Exhibit by the Beckman Center for the History of Chemistry (Publication / Beckman Center for the History of Chemistry); Mary E. Bowden; Chemical Heritage Foundation, March 1992

|SHORT DESCRIPTION=Organic chemist and discoverer of [[Woodward-Hoffmann rules]]

*{{cite journal

|DATE OF BIRTH=[[April 10]], [[1972]]

|author1=Woodward R. B. |author2=Sondheimer F. |author3=Taub D. | title= The Total Synthesis of Cortisone

|PLACE OF BIRTH=[[Boston]], [[Massachusetts]], [[USA]]

| journal=Journal of the American Chemical Society

|DATE OF DEATH=[[July 8]], [[1979]]

| year=1951

|PLACE OF DEATH=[[Cambridge, Massachusetts|Cambridge]], [[Massachusetts]], [[USA]]

| pages=4057

| volume=73

| doi=10.1021/ja01152a551

| issue= 8 |bibcode=1951JAChS..73.4057W }}

*{{cite journal

| author= George B. Kauffman

| title= Organic Synthesizer par excellence – On the 25th Anniversary of His Death

| journal=Chem. Educator

| year=2004

| pages=1–5

| volume=9

}}

*{{Nobelprize}}

*[https://web.archive.org/web/20060516234558/http://www.ch.ic.ac.uk/video/index.rss Video podcast of Robert Burns Woodward talking about cephalosporin]

*[http://www.sigmaaldrich.com/etc/medialib/docs/Aldrich/Acta/al_acta_10_01.Par.0001.File.tmp/al_acta_10_01.pdf Robert Burns Woodward: Three Score Years and Then?] [[David Dolphin]], ''[[Aldrichimica Acta]]'', '''1977''', ''10''(1), 3–9.

*[http://www.patentgenius.com/inventor/WoodwardRobertBurns.html Robert Burns Woodward Patents]

{{div col end}}

==External links==

[[Category:1917 births|Woodward, Robert B.]]

{{Wikiquote}}

[[Category:1979 deaths|Woodward, Robert B.]]

*[https://digital.sciencehistory.org/works/5d86p139h Notes from Robert Burns Woodward's Seminars] taken by Robert E. Kohler in [https://digital.sciencehistory.org/ Science History Institute Digital Collections]

[[Category:People from Boston|Woodward, Robert B.]]

* {{Nobelprize}} including the Nobel Lecture, December 11, 1965 ''Recent Advances in the Chemistry of Natural Products''

[[Category:English Americans|Woodward, Robert B.]]

[[Category:Nobel laureates in Chemistry|Woodward, Robert Burns]]

{{Nobel Prize in Chemistry Laureates 1951-1975}}

[[Category:Scottish-Americans|Woodward, Robert B.]]

{{1965 Nobel Prize winners}}

[[Category:National Medal of Science recipients|Woodward]]

{{Time Persons of the Year 1951–1975}}

{{Copley Medallists 1951–2000}}

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