A HIGHLY STEREOSELECTIVE AND PRACTICAL TOTAL SYNTHESIS OF THE TRICYCLIC BETA-LACTAM ANTIBIOTIC GV104326 (4-METHOXYTRINEM)

Authors
HANESSIAN S ROZEMA MJ
Citation
S. Hanessian et Mj. Rozema, A HIGHLY STEREOSELECTIVE AND PRACTICAL TOTAL SYNTHESIS OF THE TRICYCLIC BETA-LACTAM ANTIBIOTIC GV104326 (4-METHOXYTRINEM), Journal of the American Chemical Society, 118(41), 1996, pp. 9884-9891
Citations number
63
Categorie Soggetti
Chemistry
Journal title
Journal of the American Chemical Society → ACNP
ISSN journal
00027863
Volume
118
Issue
41
Year of publication
1996
Pages
9884 - 9891
Database
ISI
SICI code
0002-7863(1996)118:41<9884:AHSAPT>2.0.ZU;2-T
Abstract
A novel and practical total synthesis of a tricyclic beta-lactam antib iotic, GV104326 (4-methoxytrinem or Sanfetrinem) has been achieved in nine steps and about 33% overall yield from a commercially available a cetoxyazetidinone chiron. A key step in the highly diastereoselective synthesis is a protonation of a zinc enolate complex which circumvents the use of enantiomerically pure (S)-2-methoxycyclohexanone. A mechan istic rationale is presented and experimentally verified.