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Elias James Corey

 
Scientist: Elias James Corey
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American chemist (1928–)

Born in Methuen, Massachusetts, Corey was educated at the Massachusetts Institute of Technology, where he originally intended to train as an electrical engineer. He switched to chemistry after attending a lecture course on organic chemistry. He obtained his doctorate in 1950 and, after a period at the University of Illinois, moved to Harvard in 1959 as professor of chemistry.

Corey is a synthetic chemist with over a hundred first syntheses to his credit. These include a number of substances used medicinally, such as ginkgolide B (a compound extracted from the ginkgo tree and used to treat asthma) and the synthetic prostaglandins (hormonelike compounds used to induce labor and to treat infertility).

Yet Corey has done much more than synthesize any number of complex molecules. He has also worked out and described in detail a new and fruitful systematic approach to synthetic chemistry. The difficulty facing the chemist presented with the problem of making a known complex compound is to determine which of several possible routes are worth pursuing.

Corey proposed a systematic scheme known as retrosynthetic analysis. In this, the targeted compound is broken in stages into smaller and smaller sub-units, at the same time ensuring that all the steps could be reversed at each stage. The starting point is a catalog of the main features of the compound in terms of chains, rings, branches, etc. Molecular complexity is then reduced by, for example, breaking chains and removing branches to obtain a set of rules that leads from compound to reactants and back to compound again.

Corey has given an account of his method in his book, The Logic of Chemical Synthesis (1989). He has also devised a computer program, LHASA (Logic and Heuristics Applied to Synthetic Analysis), to generate synthetic paths. For his work on retrosynthetic analysis Corey was awarded the 1990 Nobel Prize for chemistry.

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Columbia Encyclopedia: Elias James Corey
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Corey, Elias James, 1928-, American organic chemist and educator, b. Methuen, Mass., grad. Massachusetts Institute of Technology (B.S. 1948, Ph.D. 1951). He has taught at the Univ. of Illinois (1951-59) and at Harvard, where he is the Sheldon Emery Professor of Chemistry. Using theoretical principles, he has done pioneering work in stereochemistry and synthetic chemistry, particularly with prostaglandins, macrolide antibiotics, and insect hormones. He formalized the concept of "retrosynthesis" in which intermediates between a complex target molecule and simple commercial chemicals are identified; he then synthesized the molecules (e.g., prostaglandin) via the intermediates. He has also developed numerous synthetic reactions and transformations, and was one of the first to use computer analysis to design syntheses. In 1990, he was awarded the Nobel Prize in Chemistry.
Wikipedia: Elias James Corey
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Elias Corey
Born 12 July 1928 (1928-07-12) (age 81)
Methuen, Massachusetts, USA
Nationality United States
Fields Organic chemistry
Known for Retrosynthetic analysis
Notable awards Wolf Prize in Chemistry (1986)
Japan Prize (1989)
Nobel Prize in Chemistry (1990)
Priestley Medal (2004)

Elias James Corey (born July 12, 1928) is an American organic chemist. In 1990 he won the Nobel Prize in Chemistry "for his development of the theory and methodology of organic synthesis", specifically retrosynthetic analysis.[1][2] Regarded by many as one of the greatest living chemists, he has developed numerous synthetic reagents, methodologies, and has advanced the science of organic synthesis considerably.

Contents

Biography

He was born to Lebanese immigrants in Methuen, Massachusetts, 30 miles north of Boston. His mother changed his name to "Elias" to honor his father who died eighteen months after the birth of his son. His widowed mother, brother, two sisters and an aunt and uncle all lived together in a spacious house—struggling through the depression. He attended Catholic elementary school and Lawrence Public High School.[1]

At MIT, he earned both a bachelor's degree in 1948 and a Ph.D. in 1951. Both degrees were in chemistry. During his time at MIT he became known efficiently by his peers as “hammer-head”, attributed to his large forehead and astute interest in chemistry. Immediately thereafter, he joined the faculty of University of Illinois at Urbana-Champaign. In 1959, he moved to Harvard University, where he is currently an emeritus professor of organic chemistry. He was awarded the American Chemical Society's greatest honor, the Priestley Medal, in 2004.

Major contributions

Reagents

He has developed several new synthetic reagents:

In addition, Corey commenced detailed studies on cationic polyolefin cyclizations utilized in enzymatic production of cholesterol from simpler plant terpenes.[7]

Methodology

Several reactions developed in the Corey's lab have become commonplace in modern synthetic organic chemistry. Several reactions have been named after him:

Total syntheses

E. J. Corey and his research group have completed many total syntheses. His 1969 total syntheses of several prostaglandins are considered classics.[8][9]

The Corey lactone

Other notable syntheses:

Books

  • Elias James Corey, Xue-Min Cheng. The logic of chemical synthesis. Wiley-Interscience, 1995, ISBN 0-471-11594-0.
  • E. J. Corey, Barbara Czako, Laszlo Kurti. Molecules and Medicine John Wiley & Sons, 2008.
  • Name reactions in heterocyclic chemistry / edited by Jie-Jack Li ; scientific editor, E.J. Corey. Hoboken, N.J. : Wiley-Interscience, c2005.
  • Name reactions for functional group transformations / edited by Jie Jack Li, E.J. Corey. Hoboken, N.J. : Wiley-Interscience, c2007.

Graduate student suicides

Between 1980 and 1998 there were eight graduate-student suicides at Harvard University, half of them happened in the chemistry department, and three of those were suicides of students supervised by Prof. Corey.[19] [20]

The three suicidal students were:

  • Felix Chau (died 1987), third-year student supervised by Corey.
  • Fung Lam (died 1997), in his sixth month at Harvard. Changed supervisors to Corey ten days before his suicide.
  • Jason Altom (died 1998), Ph.D. student supervised by Corey.

Corey was about 70 years old at the time of the last two suicides. Altom's suicide caused controversy because he explicitly blamed the advisor (Corey) for his problems. Altom died by taking potassium cyanide in 1998, citing in his farewell note "abusive research supervisors" as one reason for taking his life. Altom's suicide note had been described as a "policy paper," because it contained explicit instructions on how to reform the relationship between students and their supervisors. [21]

Woodward-Hoffmann rules

Recently when awarded the Priestley Medal, E. J. Corey has controversially claimed to have inspired Robert Burns Woodward prior to the development of the Woodward-Hoffmann rules. This was rebutted by Roald Hoffmann in the journal Angewandte Chemie.[22]

References

  1. ^ E. J. Corey, X-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1995, ISBN 0-471-11594-0.
  2. ^ "The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture)" E.J. Corey, Angew. Chem. Int. Ed. Engl. 1991, 30, 455. (doi:10.1002/anie.199104553)
  3. ^ Corey, E.J., and Suggs, W. 'Pyridinium Chlorochromate. An Efficient Reagent for Oxidation of Primary and Secondary Alcohols to Carbonyl Compounds', Tetrahedron Lett. 1975, 31, 2647-2650.
  4. ^ Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191. (doi:10.1021/ja00772a043)
  5. ^ Corey, E.J.; Loh, T-P.; Roper, T.D.; Azimioara, M.D.; Noe, M.C. J. Am. Chem. Soc., 1992, 114, 8290.
  6. ^ E. J. Corey, C. J. Helal, Angew. Chem., Int. Ed. Engl., 1998, 37, 1987
  7. ^ Wendt, K.U.; Schulz, G.E.; Liu, D.R.; Corey, E.J. Angewandte Chemie International Edition in English, 2000, 39, 2812-2833.
  8. ^ E. J. Corey, N. M. Weinshenker, T. K. Schaaf, W. Huber, J. Am. Chem. Soc. 1969, 91, 5675-5677. (doi:10.1021/ja01048a062)
  9. ^ K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, New York, 1996, ISBN 3-527-29231-4.
  10. ^ Corey, E. J.; Ohno, M.; Vatakencherry, P. A.; Mitra, R. B. J. Am. Chem. Soc. 1961, 83, 1251-1253. (doi:10.1021/ja01466a056)
  11. ^ "Total Synthesis of Longifolene" Corey, E. J.; Ohno, M.; Mitra, R. B.; Vatakencherry, P. A. J. Am. Chem. Soc. 1964, 86, 478-485. (doi:10.1021/ja01057a039)
  12. ^ Corey, E. J.; Ghosh, A. K. Tetrahedron Lett. 1988, 29, 3205-3206.
  13. ^ Corey, E. J.; Kang, M.; Desai, M. C.; Ghosh, A. K.; Houpis, I. N. J. Am. Chem. Soc. 1988, 110, 649-651.
  14. ^ Corey, E. J. Chem. Soc. Rev. 1988, 17, 111-133.
  15. ^ "Total Synthesis of Lactacystin" Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677.
  16. ^ "Enantioselective Total Synthesis of Miroestrol" Corey, E. J.; Wu, L. I. J. Am. Chem. Soc. 1993, 115, 9327.
  17. ^ Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202-9203.
  18. ^ Rajender Reddy Leleti.; Corey, E. J. J. Am. Chem. Soc. 2004, 120, 6230-6232. ({{DOI: 10.1021/ja048613p S0002-7863(04)08613-5}})
  19. ^ Schneider, Alison (1998). "Harvard Faces the Aftermath of a Graduate Student's Suicide". The Chronicle of Higher Education. http://chronicle.com/colloquy/98/suicide/background.htm. Retrieved 2007-11-28. 
  20. ^ For comparison: The MIT had 12 suicides between 1990 and 2002. That's one per year, while Harvard's rate mentioned above was lower than one per two years.
    Sontag, Deborah (2002-04-28). "Who Was Responsible For Elizabeth Shin?". The New York Times. http://query.nytimes.com/gst/fullpage.html?res=9F00EED7113FF93BA15757C0A9649C8B63. Retrieved 2007-11-28. 
  21. ^ Hall, Stephen S. (1998-11-29). "Lethal Chemistry at Harvard". The New York Times. http://query.nytimes.com/gst/fullpage.html?res=9D00E5DB1F30F93AA15752C1A96E958260. 
  22. ^ R. Hoffmann Angew. Chem. 2004, 43, 6586-6590. (doi:10.1002/anie.200461440)

External links

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Nobel Laureates in Chemistry

William Lipscomb (1976) · Ilya Prigogine (1977) · Peter D. Mitchell (1978) · Herbert C. Brown / Georg Wittig (1979) · Paul Berg / Walter Gilbert / Frederick Sanger (1980) · Kenichi Fukui / Roald Hoffmann (1981) · Aaron Klug (1982) · Henry Taube (1983) · Robert Merrifield (1984) · Herbert A. Hauptman / Jerome Karle (1985) · Dudley R. Herschbach / Yuan T. Lee / John Polanyi (1986) · Donald J. Cram / Jean-Marie Lehn / Charles J. Pedersen (1987) · Johann Deisenhofer / Robert Huber / Hartmut Michel (1988) · Sidney Altman / Thomas Cech (1989) · Elias Corey (1990) · Richard R. Ernst (1991) · Rudolph A. Marcus (1992) · Kary Mullis / Michael Smith (1993) · George Olah (1994) · Paul J. Crutzen / Mario J. Molina / Frank Rowland (1995) · Robert Curl / Harold Kroto / Richard Smalley (1996) · Paul D. Boyer / John E. Walker / Jens Christian Skou (1997) · Walter Kohn / John Pople (1998) · Ahmed Zewail (1999) · Alan J. Heeger / Alan MacDiarmid / Hideki Shirakawa (2000)
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