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

Shyla George; Srinivasarao V. Narina; Arumugam Sudalai

doi:10.1016/j.tet.2006.08.019

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

Shyla George, Srinivasarao V. Narina, Arumugam Sudalai

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34 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 language	English (US)
Pages (from-to)	10202-10207
Number of pages	6
Journal	Tetrahedron
Volume	62
Issue number	43
DOIs	https://doi.org/10.1016/j.tet.2006.08.019
State	Published - Oct 23 2006
Externally published	Yes

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.

Keywords

Asymmetric epoxidation
Asymmetric synthesis
Kinetic resolution
Tethered aminohydroxylation

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title = "A short enantioselective synthesis of (-)-chloramphenicol and (+)-thiamphenicol using tethered aminohydroxylation",

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.",

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AU - Narina, Srinivasarao V.

AU - Sudalai, Arumugam

N1 - 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.

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Y1 - 2006/10/23

N2 - 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.

AB - 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.

KW - Asymmetric epoxidation

KW - Asymmetric synthesis

KW - Kinetic resolution

KW - Tethered aminohydroxylation

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

Abstract

Bibliographical note

Keywords

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