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
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.