SYNTHETIC STUDIES ON VIRANTMYCIN .2. TOTAL SYNTHESIS OF UNNATURAL (-VIRANTMYCIN AND DETERMINATION OF ITS ABSOLUTE STEREOCHEMISTRY())

Authors
MORIMOTO Y SHIRAHAMA H
Citation
Y. Morimoto et H. Shirahama, SYNTHETIC STUDIES ON VIRANTMYCIN .2. TOTAL SYNTHESIS OF UNNATURAL (-VIRANTMYCIN AND DETERMINATION OF ITS ABSOLUTE STEREOCHEMISTRY()), Tetrahedron, 52(32), 1996, pp. 10631-10652
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
32
Year of publication
1996
Pages
10631 - 10652
Database
ISI
SICI code
0040-4020(1996)52:32<10631:SSOV.T>2.0.ZU;2-I
Abstract
The enantioselective total synthesis of (+)-virantmycin (1) has been a chieved by means of the Sharpless asymmetric epoxidation of allylic al cohol 27 followed by an intramolecular epoxide opening of the exo epox y alcohol 32 which was derived from the endo epoxy alcohol 28. The syn thesis 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 activities of the virantmycin analogs were also e xamined against influenza virus. Copyright (C) 1996 Elsevier Science L td