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.
Bibliographical noteFunding 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 2008 Elsevier B.V., All rights reserved.
- Asymmetric epoxidation
- Asymmetric synthesis
- Kinetic resolution
- Tethered aminohydroxylation