The Compiled Works of E J Corey About

The Compiled Works of E. J. Corey ØAbout E. J. Corey ØMethods/Methodology ØPublication/Syntheses

About E. J. Corey ØBorn: In July 1928 in Methuen, Massachusetts. ØEducation: Graduated from Lawrence Public High School at the age of sixteen and entered the Massachusetts Institute of Technology, just a few weeks later, in July, 1945. MIT teachers including Arthur C. Cope, John C. Sheehan, John D. Roberts and Charles Gardner Swain. In 1950, joined the University of Illinois at Urbana-Champaign(伊利诺伊香槟分校) as an Instructor in Chemistry under the distinguished chemists Roger Adams and Carl S. Marvel.

About E. J. Corey ØNotable students: Hisashi Yamamoto, J. William Suggs Ryoji Noyori 野依良治 (2001 Nobel) William L. Jorgensen K. C. Nicolaou Brian M. Stoltz Phil S. Baran David E. Cane

About E. J. Corey ØAwards : ACS Award in Pure Chemistry (1960) Chevreul Medal (1964) Fritzsche Award (1967) Intra-Science Foundation Award (1967) Harrison Howe Award (1970) Centenary Medal (1971) Ciba Foundation Medal (1972) Linus Pauling Award (1973) Dickson Prize (1973) George Ledlie Prize (1973) Remsen Award (1974) Arthur C. Cope Award (1976) Buchman Memorial Award (1978) Franklin Medal (1978) Scientific Achievement Award Medal (1979) J. G. Kirkwood Award (1980) C. S. Hamilton Award (1980)

About E. J. Corey ØAwards : Chemical Pioneer Award (1981) Lewis S. Rosenstiel Award (1981) Paul Karrer Gold Medal (1982) Tetrahedron Prize (1983) Willard Gibbs Award (1984) Paracelsus Award (1984) Madison Marshall Award (1985) V. D. Mattia Award (1985) Wolf Prize in Chemistry (1986) Silliman Award (1986) Robert Robinson Medal (1988) National Medal of Science (1988) Japan Prize (1989) Janot Medal (1990) Nobel Prize in Chemistry (1990) : Retrosynthetic analysis Roger Adams Award (1993) For. Mem. RS (1998) Priestley Medal (2004)

• Woodward–Hoffmann rules • Priestley Medal in 2004 • Corey's claim and contribution were publicly rebutted by Roald Hoffmann in the journal Angewandte Chemie

Methods • PCC (pyridinium chlorochromate) Tetrahedron Lett. 1975 31 (31): 2647 -2650 doi: 10. 1016/s 0040 -4039(00)75204 -x Tetrahedron Lett. 1978 19 (28): 2461 -2464 doi: 10. 1016/S 0040 -4039(01)94800 -2

• TBS-, TIPS-, MEM- Methods JACS 1972 94 (17): 6190– 6191 doi: 10. 1021/ja 00772 a 043 Tetrahedron Lett. 1976 17 (11): 809– 812 doi: 10. 1016/s 0040 -4039(00)92890 -9

Methods Angew. Chem. Int. Ed. 1965 4 (12): 1077– 1078 doi: 10. 1002/anie. 196510771 除疟霉素 JACS. 1982 104 (24): 6818– 6820 doi: 10. 1021/ja 00388 a 074 Methods

Methodology • Corey-Chaykovsky epoxidation and cyclopropanation 1962

Methodology • Corey-Chaykovsky epoxidation and cyclopropanation • Mechanism:

Methodology • Corey-Chaykovsky epoxidation and cyclopropanation Synthetic Applications:

Methodology • Corey-Winter olefination 1963

Methodology • Corey-Winter olefination Mechanism:

Methodology • Corey-Winter olefination Synthetic Applications:

Methodology • Corey-Fuchs alkyne synthesis 1972

Methodology • Corey-Fuchs alkyne synthesis Mechanism:

Methodology • Corey-Fuchs alkyne synthesis Synthetic Applications:

Methodology • Corey-Kim oxidation 1972

Methodology • Corey-Kim oxidation Mechanism:

Methodology • Corey-Kim oxidation Synthetic Applications:

Methodology • Corey-Kim oxidation 1972 Synthetic Applications:

Methodology • Corey-Nicolaou macrolactonization 1974

Methodology • Corey-Nicolaou macrolactonization Mechanism:

Methodology • Corey-Nicolaou macrolactonization Synthetic Applications:

Methodology • Corey-Bakshi-Shibata reduction(CBS reduction) 1981 The advantages of the CBS catalyst: Øease of preparation Øair and moisture stability Øshort reaction times Øhigh enantioselectivity, high yields Ørecovery of catalyst precursor by precipitation as the HCl salt

Methodology • Corey-Bakshi-Shibata reduction(CBS reduction) Mechanism:

Methodology • Corey-Bakshi-Shibata reduction(CBS reduction) Synthetic Applications:

Publication/Syntheses Enantioselective Total Synthesis of Aspidophytine J. Am. Chem. Soc. 1999, 121, 6771 -6772

Publication/Syntheses Enantioselective Total Synthesis of Aspidophytine Leimgruber-Batcho indole synthesis J. Am. Chem. Soc. 1999, 121, 6771 -6772

Leimgruber-Batcho indole synthesis

Publication/Syntheses Enantioselective Total Synthesis of Aspidophytine J. Am. Chem. Soc. 1999, 121, 6771 -6772

Ireland-Claisen rearrangement

Publication/Syntheses Enantioselective Total Synthesis of Aspidophytine (a) CH 3 CN, 23 °C, then TFAA, 0 °C, then Na. BH 3 CN, 23 °C, 66%. J. Am. Chem. Soc. 1999, 121, 6771 -6772

Publication/Syntheses Enantioselective Total Synthesis of Aspidophytine (b) Na. OH, Et. OH, 75 °C, 24 h, 88%. (c) K 3 Fe(CN)6, Na. HCO 3, t-Bu. OH-H 2 O 1: 2, 92%. (d) Os. O 4 (1 equiv), DMAP (2 equiv), t-Bu. OH/H 2 O (1: 1), then Na. SO 3. (e) Pb(OAc)4, Ac. OH, CH 2 Cl 2, -20 °C, 71% for two steps. (f) KHMDS, THF, -78 °C, then Ph. NTf 2, -78 °C, 54%. (g) Pd(PPh 3)4 (0. 2 equiv), Bu 3 Sn. H (8 equiv), THF, 23 °C, 1 h, 86%. J. Am. Chem. Soc. 1999, 121, 6771 -6772

Publication/Syntheses Total Synthesis of aegiceradienol J. Am. Chem. Soc. 1999, 121, 9999 -10003

Publication/Syntheses Total Synthesis of aegiceradienol Brook rearrangement JACS. 1999, 121, 9999 -10003

Publication/Syntheses Brook rearrangements Mechanism: J. Am. Chem. Soc. 1999, 121, 9999 -10003

Publication/Syntheses Total Synthesis of aegiceradienol J. Am. Chem. Soc. 1999, 121, 9999 -10003

Publication/Syntheses Total Synthesis of Antheliolide A JACS, 2006, 128, 14050 -14052 doi: 10. 1021/ja 066336 b

Publication/Syntheses Total Synthesis of Antheliolide A (b) KH, THF, -40 °C, 30 min; then Bu 3 Sn. CH I at 40 °C; 0 °C, 16 h; 2 (a) 2 -equiv t-Bu. Li, 2, Et 2 O, -78 °C; 20 °C, 6 h; then 3, -78 °C, 2 h; (90%) (c) n-Bu. Li, THF, -78 °C, 3 h (61% from 4)

Publication/Syntheses Total Synthesis of Antheliolide A Org. Lett. 2002, 4, 2441 -2443

Publication/Syntheses Total Synthesis of Antheliolide A