Tetrahedron letters

A facile method for synthesis of (R)-(−)-and (S)-(+)-homocitric acid lactones and related α-hydroxy dicarboxylic acids from d-or l-malic acid

PF Xu, T Matsumoto, Y Ohki, K Tatsumi

Index: Xu, Peng-Fei; Matsumoto, Tsuyoshi; Ohki, Yasuhiro; Tatsumi, Kazuyuki Tetrahedron Letters, 2005 , vol. 46, # 22 p. 3815 - 3818

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Citation Number: 17

Abstract

We report here a simple and convenient route for the stereoselective synthesis of (R)-(−)- and (S)-(+)-homocitric acid lactones, which play very important roles in biochemistry. The method involves only three steps, starting from the readily available methyl 3-iodopropionate and d-malic acid or l-malic acid, respectively. The stereoconfiguration of the target molecules has been achieved via a self-regeneration approach with over 98% ...

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