Robert Burns Woodward

Robert Burns Woodward (April 10, 1917 – July 8, 1979) was an American organic chemist. He is considered by many to be the preeminent organic chemist of the twentieth century,[2] having made many key contributions to the subject, especially in the synthesis of complex natural products and the determination of their molecular structure. He also worked closely with Roald Hoffmann on theoretical studies of chemical reactions. He was awarded the Nobel Prize in Chemistry in 1965.

Robert Burns Woodward
Robert Woodward Nobel
BornApril 10, 1917
DiedJuly 8, 1979 (aged 62)
CitizenshipUnited States
Alma materMIT (S.B., Ph.D.)
Known for
Awards
Scientific career
FieldsOrganic chemistry
InstitutionsHarvard University
Doctoral advisorJames Flack Norris
Avery Adrian Morton
Doctoral students

Early life and education

Woodward was born in Boston, Massachusetts, to Margaret (née Burns, an immigrant from Scotland, and a descendant of Robert Burns, the poet) and Arthur Chester Woodward, son of Roxbury, Massachusetts apothecary, Harlow Elliot Woodward. When Robert was one year old, his father died in the flu pandemic of 1918.

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,[3] 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 [4]), 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 doctorate, when his classmates were still graduating with their bachelor's degrees.[5] Woodward's doctoral work involved investigations related to the synthesis of the female sex hormone estrone.[6] MIT required that graduate students have research advisors. Woodward's advisors were James Flack Norris and Avery Adrian Morton, 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.

Research and career

Early work

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 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.

Later work and its impact

Robert Burns Woodward in 1965
Woodward talked about Chlorophyll in 1965

Culminating in the 1930s, the British chemists Christopher Ingold and 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

During the late 1940s, Woodward synthesized many complex natural products including quinine, cholesterol, cortisone, strychnine, lysergic acid, reserpine, chlorophyll, cephalosporin, and colchicine.[7] 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 '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.

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 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 thiazolidineoxazolone structure proposed by 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.

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. 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.

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.[8] This marked the beginning of the field of transition metal organometallic chemistry which grew into an industrially very significant field.[9] Wilkinson won the Nobel Prize for this work in 1973, along with Ernst Otto Fischer.[10] 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.[11]

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.[12] 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.

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 (see also palytoxin, synthesized by the research group of Yoshito Kishi, one of Woodward's postdoctoral students). As of 2016, no other total synthesis of Vitamin B12 has been published.

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 reactions.[13] Woodward formulated his ideas (which were based on the symmetry properties of molecular orbitals) 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

While at Harvard, Woodward took on the directorship of the Woodward Research Institute, based at Basel, Switzerland, in 1963.[14] He also became a trustee of his alma mater, MIT, from 1966 to 1971, and of the Weizmann Institute of Science in Israel.

Woodward died in Cambridge, Massachusetts from a 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.

Publications

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.

Some of his best-known students include Robert M. Williams (Colorado State), Harry Wasserman (Yale), Yoshito Kishi (Harvard), Stuart Schreiber (Harvard), William R. Roush (Scripps-Florida), Steven A. Benner (UF), 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).

Woodward had an encyclopaedic knowledge of chemistry, and an extraordinary memory for detail.[15] 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.[15]

Honors and awards

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:

Honorary degrees

Woodward also received over twenty honorary degrees,[18] including honorary doctorates from the following universities:

Personal life

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 Muller, an artist and technician whom he met at 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).[5]

Idiosyncrasies

His lectures frequently lasted for three or four hours.[4] 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.[19] 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.[4] 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. He detested exercise, could get along with only a few hours of sleep every night, was a heavy smoker, and enjoyed Scotch whisky and martinis.[1][20]

References

  1. ^ a b c Todd, L.; Cornforth, J.; T., A. R.; C., J. W. (1981). "Robert Burns Woodward. 10 April 1917-8 July 1979". Biographical Memoirs of Fellows of the Royal Society. 27 (0): 628–695. doi:10.1098/rsbm.1981.0025. ISSN 0080-4606.
  2. ^ Elkan Blout (2001). "Robert Burns Woodward". Biographical Memoirs of the National Academy of Sciences. 80. | url = http://www.nasonline.org/publications/biographical-memoirs/memoir-pdfs/woodward-robert-b.pdf
  3. ^ Putnam, Robert C. (2001). Benfey, Otto Theodor; Turnbull Morris, Peter John, eds. Reminiscences From Junior High School. Robert Burns Woodward: Architect and Artist in the World of Molecules. Chemical Heritage Foundation. p. 12.
  4. ^ a b c 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 link.
  5. ^ a b The Nobel Prize in Chemistry 1965 - Robert B. Woodward Biography Nobelprize.org
  6. ^ A synthetic attack on the oestrone problem PhD dissertation
  7. ^ "Chlorophyll". The New York Times. July 3, 1960. Retrieved 2012-10-13. 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. ...
  8. ^ Wilkinson, G.; Rosenblum, M.; Whiting, M. C.; Woodward, R. B. (1952). "The Structure of Iron Bis-Cyclopentadienyl". J. Am. Chem. Soc. 74 (8): 2125–2126. doi:10.1021/ja01128a527.
  9. ^ Federman Neto, A.; Pelegrino, A. C.; Darin, V. A. (2004). "Ferrocene: 50 Years of Transition Metal Organometallic Chemistry — From Organic and Inorganic to Supramolecular Chemistry". ChemInform. 35 (43). doi:10.1002/chin.200443242.
  10. ^ "The Nobel Prize in Chemistry 1973". nobelprize.org. Retrieved 12 September 2010.
  11. ^ Werner, H. (2008). Landmarks in Organo-Transition Metal Chemistry: A Personal View. Springer Science. pp. 161–163. ISBN 978-0-387-09847-0.
  12. ^ https://www.nobelprize.org/nomination/archive/show_people.php?id=10302
  13. ^ Hoffmann, R.; Woodward, R. B. (1970). "Orbital Symmetry Control of Chemical Reactions". Science (published Feb 6, 1970). 167 (3919): 825–831. Bibcode:1970Sci...167..825H. doi:10.1126/science.167.3919.825. PMID 17742608.
  14. ^ Craig, G. Wayne (2011). "The Woodward Research Institute, Robert Burns Woodward (1917–1979) and Chemistry behind the Glass Door". Helvetica Chimica Acta. 94 (6): 923. doi:10.1002/hlca.201100077.
  15. ^ a b Roberts, J. (1990). The Right Place at the Right Time. American Chemical Society. ISBN 978-0-8412-1766-9.
  16. ^ Awards North Jersey Section American Chemical Society - see section Current & Past Recipients of the Leo Hendrik Baekeland Award
  17. ^ American Chemical Society - Chicago Section
  18. ^ Blout, Elkan. "Robert Burns Woodward 1917–1979: A Biographical Memoir" (PDF). National Academy of Sciences. The National Academy Press. Retrieved 15 January 2017.
  19. ^ (in French)Introduction à la chimie quantique Philippe Hiberty and Nguyên Trong Anh, Editions Ecole Polytechnique Renaud-Bray (2008) p.115 ISBN 2730214852
  20. ^ Robert Burns Woodward Archived 2012-06-03 at WebCite.

Bibliography

External links

Cholesterol total synthesis

Cholesterol total synthesis in chemistry describes the total synthesis of the complex biomolecule cholesterol and is considered a great scientific achievement. The research group of Robert Robinson with John Cornforth (Oxford University) published their synthesis in 1951 and that of Robert Burns Woodward with Franz Sondheimer (Harvard University) in 1952. Both groups competed for the first publication since 1950 with Robinson having started in 1932 and Woodward in 1949. According to historian Greg Mulheirn the Robinson effort was hampered by his micromanagement style of leadership and the Woodward effort was greatly facilitated by his good relationships with chemical industry. Around 1949 steroids like cortisone were produced from natural resources but expensive. Chemical companies Merck & Co. and Monsanto saw commercial opportunities for steroid synthesis and not only funded Woodward but also provided him with large quantities of certain chemical intermediates from pilot plants. Hard work also helped the Woodward effort: one of the intermediate compounds was named Christmasterone as it was synthesized on Christmas Day 1950 by Sondheimer.

Other cholesterol schemes have also been developed: racemic cholesterol was synthesized in 1966 by W.S. Johnson, the enantiomer of natural cholesterol was reported in 1996 by Rychnovsky and Mickus , in 2002 by Jiang & Covey and again in 2008 by Rychnovsky and Belani .

Ernest Wenkert

Ernest Wenkert, (16 October 1925 – 20 June 2014) was an Austrian-born American chemist.

Wenkert received B.S. (1945) and M.S. (1947) degrees in chemistry from the University of Washington. In 1951, he was awarded a Ph.D. degree in organic chemistry from Harvard University, where he studied under Robert Burns Woodward. From 1951, he served as a faculty member at Iowa State University, and was in 1961 appointed as the Herman T. Briscoe Professor of Chemistry at Indiana University. In 1974, he took the position as E.D. Butcher Professor of Chemistry at Rice University, also serving as chair of the chemistry department. In 1980, he moved to the University of California, San Diego, where he stayed until his retirement in 1994.

George Ledlie Prize

The George Ledlie Prize is awarded by the "President and Fellows of Harvard College" for contributions to science.

Ian Fleming (chemist)

Ian Fleming (born 1935) is an English organic chemist, and an emeritus professor of the University of Cambridge, and an emeritus fellow of Pembroke College, Cambridge. He was the first to determine the full structure of chlorophyll (in 1967) and was involved in the development of the synthesis of cyanocobalamin by Robert Burns Woodward. He has made major contributions to the use of organosilicon compounds for stereospecific syntheses; reactions which have found application in the synthesis of natural compounds. He is also a prolific author, and has written a number of textbooks, encyclopedia chapters and influential review articles.

John Scott Medal

John Scott Award, created in 1816 as the John Scott Legacy Medal and Premium, is presented to men and women whose inventions improved the "comfort, welfare, and happiness of human kind" in a significant way. Since 1919 the Board of Directors of City Trusts of Philadelphia provide this award, recommended by an advisory committee.In 1822 the first awards were given to thirteen people by the Philadelphia Society for Promoting Agriculture entrusted by the "Corporation of the city of Philadelphia".The druggist John Scott of Edinburgh organized a $4,000 fund which, after his death in 1815 was administered by a merchant until the first award, a copper medal and "an amount not to exceed twenty dollars", was given in 1822. (At the time, $20 could buy one ox or a 12-volume encyclopedia.) Several hundred recipients have since been selected by the City Council of Philadelphia, which decides from the annual list of nominees made by the Franklin Institute.

Most awards have been given for inventions in science and medicine. Famous

recipients include

Thomas Edison,

Nikola Tesla,

Marie Curie,

the Wright brothers,

Guglielmo Marconi,

Irving Langmuir,

Alexander Fleming,

William T. Bovie,

Frederick G. Banting,

Edgar Sharp McFadden,

John Bardeen,

Edwin Land,

Luis W. Alvarez,

Glenn Seaborg,

Jonas Salk,

Robert Burns Woodward,

Humberto Fernandez Moran,

James Black,

Benoît Mandelbrot,

Ralph L. Brinster,

Richard E. Smalley, and

Kary B. Mullis.

List of Fellows of the Royal Society elected in 1956

Fellows of the Royal Society who were elected in 1956.

Otto Theodor Benfey

Otto Theodor Benfey (born 31 October 1925) is a chemist and historian of science. Sent to England to escape Nazi Germany at age 10, he completed his education as a chemist at University College London before moving to the United States. A Quaker and a pacifist, Benfey taught at Haverford College, Earlham College, and Guilford College, retiring in 1988 as the Dana Professor of Chemistry and History of Science, Emeritus.

Benfey is known for his work on chemical education and the history of science. He edited the ACS-sponsored high school magazine Chemistry for fifteen years. His translations include The Japanese and Western Science by Masao Watanabe, The History of the International Chemical Industry by Fred Aftalion, and My 132 Semesters of Chemistry Studies by Vladimir Prelog. His books include From vital force to structural formulas (1964), Introduction to Organic Reaction Mechanisms (1970), and Robert Burns Woodward. Architect and Artist in the World of Molecules (2001).

Pierre Deslongchamps

Pierre Deslongchamps (born 1938 in Saint-Lin-Laurentides, Quebec) is a Canadian chemist, and professor at Université de Sherbrooke.

He was a 1979 Guggenheim Fellow.

Quincy High School (Massachusetts)

Quincy High School (QHS) is a public secondary school located on Coddington Street in Quincy, Massachusetts. It doubles as one of two high schools in the city of Quincy and as the vocational center. Quincy's mascot is known as the 'Presidents' and their school colors are Blue & White.

Quinine total synthesis

The total synthesis of quinine, a naturally-occurring antimalarial drug, was developed over a 150-year period. The development of synthetic quinine is considered a milestone in organic chemistry although it has never been produced industrially as a substitute for natural occurring quinine. The subject has also been attended with some controversy: Gilbert Stork published the first stereoselective total synthesis of quinine in 2001, meanwhile shedding doubt on the earlier claim by Robert Burns Woodward and William Doering in 1944, claiming that the final steps required to convert their last synthetic intermediate, quinotoxine, into quinine would not have worked had Woodward and Doering attempted to perform the experiment. A 2001 editorial published in Chemical & Engineering News sided with Stork, but the controversy was eventually laid to rest once and for all when Williams and coworkers successfully repeated Woodward's proposed conversion of quinotoxine to quinine in 2007.

Sandwich compound

In organometallic chemistry, a sandwich compound is a chemical compound featuring a metal bound by haptic covalent bonds to two arene ligands. The arenes have the formula CnHn, substituted derivatives (for example Cn(CH3)n) and heterocyclic derivatives (for example BCnHn+1). Because the metal is usually situated between the two rings, it is said to be "sandwiched". A special class of sandwich complexes are the metallocenes.

The term sandwich compound was introduced in organometallic nomenclature in the mid-1950s in a report by J. D. Dunitz, L. E. Orgel and R. A. Rich, who confirmed the structure of ferrocene by X-ray crystallography. The correct structure had been proposed several years previously by Robert Burns Woodward and, separately, by Ernst Otto Fischer. The structure helped explain puzzles about ferrocene's conformers, the molecule features an iron atom sandwiched between two parallel cyclopentadienyl rings. This result further demonstrated the power of X-ray crystallography and accelerated the growth of organometallic chemistry.

T. R. Govindachari

Tuticorin Raghavachari Govindachari (1915–2001), popularly known as TRG, was an Indian natural product chemist, academic, institution builder and the principal of Presidency College, Chennai. He was known for his studies on the synthesis of isoquinolines and phenanthridines and his contributions in elucidating the structure of several plant constituents. He was an elected fellow of the Indian Academy of Sciences and the Indian National Science Academy and was the nominator of Robert Burns Woodward who won the 1965 Nobel Prize in Chemistry. The Council of Scientific and Industrial Research, the apex agency of the Government of India for scientific research, awarded him the Shanti Swarup Bhatnagar Prize for Science and Technology, one of the highest Indian science awards, in 1960, for his contributions to chemical sciences, making him the first recipient of the award in the chemical sciences category.

Tetrahedron Prize

The Tetrahedron Prize for Creativity in Organic Chemistry or Bioorganic and Medicinal Chemistry is awarded annually by Elsevier, the publisher of Tetrahedron Publications. It was established in 1980 and named in honour of the founding co-chairmen of these publications, Professor Sir Robert Robinson and Professor Robert Burns Woodward. The prize consists of a gold medal, a certificate, and a monetary award of US $15,000.

Total synthesis

Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes it from semisynthesis. The target molecules can be natural products, medicinally important active ingredients, or organic compounds of theoretical interest. Often the aim is to discover new route of synthesis for a target molecule for which there already exist known routes. Sometimes no route exists and the chemist wishes to find a viable route for the first time. One important purpose of total synthesis is the discovery of new chemical reactions and new chemical reagents.

William R. Roush

William R. Roush is an American organic chemist. He was born on February 20, 1952 in Chula Vista, California. Roush studied chemistry at the University of California Los Angeles (B.S. 1974) and Harvard University (Ph.D. 1977 under Robert Burns Woodward). Following a year postdoctoral appointment at Harvard, he joined that faculty at the Massachusetts Institute of Technology. In 1987, Dr. Roush moved to Indiana University and was promoted to Professor in 1989 and Distinguished Professor in 1995. Two years later, he moved to the University of Michigan in Ann Arbor and served as the Warner Lambert/Parke Davis Professor of Chemistry. He served as chair of the University of Michigan's Department of Chemistry from 2002-2004. In 2004 Professor Roush relocated with his group to the Jupiter, Florida campus of the Scripps Research Institute (TSRI) where he is currently an emeritus professor.

Roush was active in the field of organic chemistry with research interests including natural product synthesis, methods development and medicinal chemistry. He is known for his stereochemical studies and synthetic applications of the intramolecular Diels-Alder reaction and his work in the area of asymmetric and acyclic diastereoselective synthesis, specifically the use of tartrate ester modified allylboronates and other allylmetal compounds for the aldol-like construction of propionate-derived systems. He has also made important contributions the synthesis of deoxyglycosides and polyhydroxylated natural products, and to the design and synthesis of inhibitors of cysteine proteases targeting important human pathogens (e.g., Trypanosoma, Plasmodium and Entamoeba species).

William von Eggers Doering

William von Eggers Doering (June 22, 1917 – January 3, 2011) was a Professor Emeritus at Harvard University and the former Chair of its Chemistry Department. Prior to joining the Faculty at Harvard, he was a member of the Chemistry Faculties of Columbia University (1942–1952) and Yale (1952–1968).

He is known in the field of organic chemistry for his work on quinine total synthesis with Robert Burns Woodward. Having published his first scientific paper in 1939 and his last in 2008, he holds the rare distinction of having authored scholarly articles in eight different decades. In 1989, he received the "James Flack Norris Award in Physical Organic Chemistry" of the American Chemical Society and in 1990 the Robert A. Welch Award in Chemistry.Some of his major contributions include recognition of the aromatic nature of the tropylium cation, investigation of the stereochemistry of the Cope rearrangement, and pioneering work in carbene chemistry, including the discovery of dichlorocarbene. Some other notable work include the synthesis of fulvalene, the discoveries of the Doering-LaFlamme allene synthesis and the Parikh-Doering oxidation, prediction of the existence of bullvalene as a fluxional molecule, and elucidation of the mechanism of the Baeyer–Villiger oxidation. Together with H. H. Zeiss, he proposed the Doering-Zeiss mechanistic hypothesis for solvolysis reactions. He first articulated the notion that cyclic systems with (4n + 2) π-electrons exhibit aromatic stability (the modern form of Hückel's rule) and coined the term "carbene" in collaboration with Woodward and Winstein during a nocturnal cab ride in Chicago.

Woodward's rules

Woodward's rules, named after Robert Burns Woodward and also known as Woodward–Fieser rules (for Louis Fieser) are several sets of empirically derived rules which attempt to predict the wavelength of the absorption maximum (λmax) in an ultraviolet–visible spectrum of a given compound. Inputs used in the calculation are the type of chromophores present, the substituents on the chromophores, and shifts due to the solvent. Examples are conjugated carbonyl compounds, conjugated dienes, and polyenes.

Woodward cis-hydroxylation

The Woodward cis-hydroxylation (also known as the Woodward reaction) is the chemical reaction of alkenes with iodine and silver acetate in wet acetic acid to form cis-diols.(convertion of olefin into cis-diol)

The reaction is named after its discoverer, Robert Burns Woodward.

This reaction has found application in steroid synthesis.

Yoshito Kishi

Yoshito Kishi (岸 義人, Kishi Yoshito, born 13 April 1937 in Nagoya, Japan) is the Morris Loeb Professor of Chemistry at Harvard University. He is known for his contributions to the sciences of organic synthesis and total synthesis.

Kishi was born in Nagoya, Japan and attended Nagoya University where he obtained both his BS and PhD degrees. He was a postdoctoral research fellow at Harvard University where he worked with Robert Burns Woodward. From 1966 through 1974, he was a professor of chemistry at Nagoya University. Since 1974, Kishi has been a professor of chemistry at Harvard University.

Kishi's research has focused on the total synthesis of complex natural products. The accomplishments of his research group include the total syntheses of palytoxin, mycolactones, halichondrins, saxitoxin, tetrodotoxin, geldanamycin, batrachotoxin and many others. Kishi has also contributed to the development of new chemical reactions including the Nozaki–Hiyama–Kishi reaction.

1901–1925
1926–1950
1951–1975
1976–2000
2001–present
1927–1950
1951–1975
1976–2000
2001–present
Copley Medallists (1951–2000)

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