Advanced Synthesis & Catalysis

Synthesis and Highly Stereoselective Hydrogenation of the Statin Precursor Ethyl (5S)??5, 6??Isopropylidenedioxy??3??oxohexanoate

VI Tararov, G König, A Börner

Index: Tararov, Vitali I.; Koenig, Gerd; Boerner, Armin Advanced Synthesis and Catalysis, 2006 , vol. 348, # 18 p. 2633 - 2644

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Citation Number: 15

Abstract

Abstract A search for the large-scale preparation of (5S)-5, 6-(isopropylidenedioxy)-3- oxohexanoates (2)–a key intermediate in the synthesis of pharmacologially important statins– starting from (S)-malic acid is described. The synthesis of the required initial compound methyl (3S)-3, 4-(isopropylidenedioxy) butanoate (1) by Moriwake's reduction of dimethyl (S)- malate (3) has been improved. Direct 2-C chain elongation of ester 1 using the lithium ...