Tetrahedron

Synthetic studies on virantmycin. 2. Total synthesis of unnatural (+)-virantmycin and determination of its absolute stereochemistry

Y Morimoto, H Shirahama

Index: Morimoto, Yoshiki; Shirahama, Haruhisa Tetrahedron, 1996 , vol. 52, # 32 p. 10631 - 10652

Full Text: HTML

Citation Number: 34

Abstract

The enantioselective total synthesis of (+)-virantmycin (1) has been achieved by means of the Sharpless asymmetric epoxidation of allylic alcohol 27 followed by an intramolecular epoxide opening of the exo epoxy alcohol 32 which was derived from the endo epoxy alcohol 28. The synthesis of (+)-1 has established that the absolute configuration of the natural product (−)-1 is shown to be 2R, 3R at the two chiral centers. Further, antiviral ...