An organocatalytic approach to the construction of chiral oxazolidinone rings and application in the synthesis of antibiotic linezolid and its analogues

Lirong Song; Xiaobei Chen; Shilei Zhang; Haoyi Zhang; Ping Li; Guangshun Luo; Wenjing Liu; Wenhu Duan; Wei Wang

doi:10.1021/ol802333n

An organocatalytic approach to the construction of chiral oxazolidinone rings and application in the synthesis of antibiotic linezolid and its analogues

Org Lett. 2008 Dec 4;10(23):5489-92. doi: 10.1021/ol802333n.

Authors

Lirong Song¹, Xiaobei Chen, Shilei Zhang, Haoyi Zhang, Ping Li, Guangshun Luo, Wenjing Liu, Wenhu Duan, Wei Wang

Affiliation

¹ Department of Pharmaceutical Sciences, School of Pharmacy, East China University of Science & Technology, Shanghai 200237, People's Republic of China.

PMID: 19006317
DOI: 10.1021/ol802333n

Abstract

An efficient, catalytic asymmetric approach to antibacterial agent linezolid has been developed. The route features organocatalytic, highly enantioselective aldol and Beckman rearrangement reactions. The strategy has also been successfully applied for the preparation of new alpha-substituted analogues with high enantio- and diastereoselectivity.

Publication types

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

MeSH terms

Acetamides / chemical synthesis*
Acetamides / chemistry*
Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry*
Catalysis
Linezolid
Oxazolidinones / chemical synthesis
Oxazolidinones / chemistry*
Stereoisomerism

Substances

Acetamides
Anti-Bacterial Agents
Oxazolidinones
Linezolid