Stereoselective synthesis of the axially chiral A-B ring system of vancomycin utilizing a planar chiral arene chromium complex

K Kamikawa; A Tachibana; S Sugimoto; M Uemura

doi:10.1021/ol010076f

Stereoselective synthesis of the axially chiral A-B ring system of vancomycin utilizing a planar chiral arene chromium complex

Org Lett. 2001 Jun 28;3(13):2033-6. doi: 10.1021/ol010076f.

Authors

K Kamikawa¹, A Tachibana, S Sugimoto, M Uemura

Affiliation

¹ Department of Chemistry, Faculty of Integrated Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.

PMID: 11418042
DOI: 10.1021/ol010076f

Abstract

[reaction: see text] The axial biaryl ring system of vancomycin was stereoselectively synthesized by utilizing a planar chiral tricarbonyl(arylhalide)chromium complex. Both enantiomers of the planar chiral (arylbromide)chromium complexes, (+)-9 and ent-(-)-9, can be stereoselectively transferred to an absolutely identical key intermediate 23 for the vancomycin A-B ring system by the diastereoselective Suzuki-Miyaura cross-coupling reaction as key step.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Chromium Compounds / chemistry
Molecular Conformation
Vancomycin / chemical synthesis*
Vancomycin / chemistry

Substances

Anti-Bacterial Agents
Chromium Compounds
Vancomycin