Synthesis of chiral pyrrolidine derivatives from (S)-pyroglutamic acid. II. 4-(hydroxymethyl)-3-azabicyclo[3.1.0]hexan-2-ones and 5,S-disubstituted 2-pyrrolidinones

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 1, 1997, Pages 36-42

  Nagasaka, Tatsuo ^a   Imai, Tomoko ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

(S) pyroglutamic acid; 2 pyrrolidinone; 5,5 disubstituted; azabicyclo 3.1.0 hexane; chiral pyrrolidine; N,O acetal; unsaturated lactam

Indexed keywords

4 (HYDROXYMETHYL) 1 METHYL 3 AZABICYCLO[3.1.0]HEXAN 2 ONE; 4 (HYDROXYMETHYL) 3 AZABICYCLO[3.1.0]HEXAN 2 ONE; 5 (HYDROXYMETHYL) 5 [2 (METHOXYCARBONYL)ETHYL] 2 PYRROLIDINONE; 5 (HYDROXYMETHYL) 5 [2 (METHOXYCARBONYL)ETHYL] 3 PYRROLIN 2 ONE; LACTAM DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 0031024485     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.36     Document Type: Article

References (14)

1. Part I: Nagasaka T., Imai T., Chem. Pharm. Bull., 43, 1081-1088 (1995).
2. A part of this work has been reported as a communication: Nagasaka T., Imai T., Heterocycles, 41, 1927-1930 (1995).
3. Hamada Y., Kawai A., Kohno Y., Hara O., Shioiri T., J. Am. Chem. Soc., 111, 1524-1525 (1989).
4. Baldwin J. E., Moloney M. G., Shim S. B., Tetrahedron Lett., 32, 1379-1380 (1991); Hanessian S., Ratovelomanana V., Syn. Lett., 1990, 501-503.
5. Baldwin J. E., Moloney M. G., Shim S. B., Tetrahedron Lett., 32, 1379-1380 (1991); Hanessian S., Ratovelomanana V., Syn. Lett., 1990, 501-503.
6. Corey E. J., Chaykovsky M., J. Am. Chem. Soc., 87, 1353-1364 (1965).
7. Shimamoto K., Ishida M., Shinozaki H., Ohfune Y., J. Org. Chem., 56, 4167-4176 (1991); Ohfune Y., Shinozaki H., "Drug Design for Neuroscience," ed. by Kozikowski A. P., Ravan Press, New York, 1993, p. 261.
8. Shimamoto K., Ishida M., Shinozaki H., Ohfune Y., J. Org. Chem., 56, 4167-4176 (1991); Ohfune Y., Shinozaki H., "Drug Design for Neuroscience," ed. by Kozikowski A. P., Ravan Press, New York, 1993, p. 261.
9. The alternative cyclopropanation of the α,β-unsaturated γ-lactam with diazomethane in the presence of a catalytic amount of palladium diacetate has appeared in ref. 6; Epoxidation of 2 with lithium tert-butylhydroperoxide was not significantly efficient for stereocontrol and yield was only moderate (46%); Griffart-Brunet D., Langlois N., Tetrahedron Lett., 35, 119-122 (1994).
10. This idea is analogous to Seebach's method using 2-tert-butyl-1-aza-3-oxa-bicyclo[3.3.0]octan-4-one; Seebach D., Boes M., Naef R., Schweizer W. B., J. Am. Chem. Soc., 105, 5390-5398 (1983). During the course of this work, the total synthesis of (+)-lactacystin from (R)-pyroglutamate, with key reactions similar to ours, was reported; Uno H., Baldwin J. E., Russell A. T., J. Am. Chem. Soc., 116, 2139-2140 (1994).
11. This idea is analogous to Seebach's method using 2-tert-butyl-1-aza-3-oxa-bicyclo[3.3.0]octan-4-one; Seebach D., Boes M., Naef R., Schweizer W. B., J. Am. Chem. Soc., 105, 5390-5398 (1983). During the course of this work, the total synthesis of (+)-lactacystin from (R)-pyroglutamate, with key reactions similar to ours, was reported; Uno H., Baldwin J. E., Russell A. T., J. Am. Chem. Soc., 116, 2139-2140 (1994).
12. Kuehne M.E., Bornmann W. G., Parsons W. H., Spitzer T. D., Blount J. F., Zubieta J., J. Org. Chem., 53, 3439-3450 (1988); Georg G. I., Guan X., Tetrahedron Lett., 33, 17-20 (1992).
13. Kuehne M.E., Bornmann W. G., Parsons W. H., Spitzer T. D., Blount J. F., Zubieta J., J. Org. Chem., 53, 3439-3450 (1988); Georg G. I., Guan X., Tetrahedron Lett., 33, 17-20 (1992).
14. Nagasaka T., Momose K., Hamaguchi F., Yamada K., Yamada H., Suzuki Y., Yakugaku Zasshi, 112, 100-107 (1992).