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Asymmetric synthesis of the antibiotic (+)-thiamphenicol using cis-N-( p-toluenesulfinyl)aziridine 2-carboxylic acids
Journal article   Peer reviewed

Asymmetric synthesis of the antibiotic (+)-thiamphenicol using cis-N-( p-toluenesulfinyl)aziridine 2-carboxylic acids

Franklin A Davis and Ping Zhou
Tetrahedron letters, v 35(41), pp 7525-7528
1994

Abstract

A concise, highly efficient asymmetric synthesis of aminopropanediol (1R,2R)-(−)- 3, precursor to the broad spectrum antibiotics thiamphenicol/florfenicol 1 2 , was prepared in two steps from cis-aziridine 2-carboxylic acid (2S,3S)-(−)- 5. The key intermediate in the asymmetric synthesis of the broad spectrum antibiotic thiamphenicol (+)- 1, aminopropanediol (−)- 3, was prepared in two steps from cis-N-( p-toluenesulfinyl)aziridine 2-carboxylic acid (−)- 5.

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Web of Science research areas
Chemistry, Organic
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