The Journal of organic chemistry

Diastereoselective synthesis of all eight L-hexoses from L-ascorbic acid

L Ermolenko, NA Sasaki

Index: Ermolenko, Ludmila; Sasaki, N. Andre Journal of Organic Chemistry, 2006 , vol. 71, # 2 p. 693 - 703

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Citation Number: 41

Abstract

A novel versatile method for the synthesis of all eight diastereomerically pure l-hexoses was developed. l-Ascorbic acid was converted to two diastereomers A. These α-hydroxy esters were transformed into four γ-alkoxy-α, β-unsaturated esters C via the intermediates B and subsequent Wittig olefination reactions. Each one of compounds C was subjected to dihydroxylation to provide a set of two diols D. Anti/syn-differentiation in diol formation was ...