A VERSATILE SYNTHESIS OF BETA-AMINO ACIDS USING THE NICHOLAS REACTION.2. FORMAL TOTAL SYNTHESIS OF THIENAMYCIN

Authors
JACOBI PA ZHENG WJ
Citation
Pa. Jacobi et Wj. Zheng, A VERSATILE SYNTHESIS OF BETA-AMINO ACIDS USING THE NICHOLAS REACTION.2. FORMAL TOTAL SYNTHESIS OF THIENAMYCIN, Tetrahedron letters, 34(16), 1993, pp. 2585-2588
Citations number
9
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
16
Year of publication
1993
Pages
2585 - 2588
Database
ISI
SICI code
0040-4039(1993)34:16<2585:AVSOBA>2.0.ZU;2-0
Abstract
Homochiral acetylenic acid 26, prepared using the Schreiber modificati on of the Nicholas reaction, has been converted to beta-amino acid der ivative 28 by a two step sequence involving Curtius rearrangement foll owed by oxidative cleavage of the acetylenic bond. Amino acid derivati ve 28 was then converted to thienamycin (12) precursor 30 by cyclizati on with DCC followed by epimerization.