A short enantioselective synthesis of (-)-chloramphenicol and (+)-thiamphenicol using tethered aminohydroxylation

Shyla George, Srinivasarao V. Narina, Arumugam Sudalai

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

An efficient enantioselective synthesis of (-)-chloramphenicol (1) and (+)-thiamphenicol (2) is described. These antibiotics have been synthesized from commercially available 4-nitrobenzaldehyde and 4-(methylthio)benzaldehyde, respectively, using tethered aminohydroxylation and Sharpless asymmetric epoxidation as the chirality inducing steps.

Original languageEnglish (US)
Pages (from-to)10202-10207
Number of pages6
JournalTetrahedron
Volume62
Issue number43
DOIs
StatePublished - Oct 23 2006

Bibliographical note

Funding Information:
S.G. and S.V.N. thank CSIR, New Delhi for the award of research fellowships. The authors are thankful to Dr. B. D. Kulkarni, Head, CEPD, for his support and encouragement.

Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.

Keywords

  • Asymmetric epoxidation
  • Asymmetric synthesis
  • Kinetic resolution
  • Tethered aminohydroxylation

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