First synthesis of both enantiomers of the biotin vitamer 8-amino-7-oxopelargonic acid

…, T Le Gall, C Mioskowski, O Ploux, A Marquet

Index: Lucet, Denis; Le Gall, Thierry; Mioskowski, Charles; Ploux, Olivier; Marquet, Andree Tetrahedron Asymmetry, 1996 , vol. 7, # 4 p. 985 - 988

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Citation Number: 32

Abstract

A short and efficient synthesis of both 8-amino-7-oxopelargonic acid enantiomers from d or l- alanine is presented. The key step of this first chemical synthesis is the non-racemizing Horner-Wadsworth-Emmons reaction of a β-ketophosphonate 3 and benzyl 4- formylbutanoate. The growth-promoting effect of the enantiomers was tested on Saccharomyces cerevisiae.