An Asymmetric Synthesis of Rosuvastatin Calcium

Abstract

A novel asymmetric synthesis of a (3R,5S)-dihydroxyhexanoic ester is described. The ester, which serves as the precursor for generating the side chain of rosuvastatin, is synthesized from d-glucose and subsequently coupled, under Wittig olefination conditions, with a phosphonium ylide derived from an appropriately substituted pyrimidine moiety. The coupling results in the formation of a precursor containing all the structural features of rosuvastatin. This precursor is converted into rosuvastatin calcium following a well-established procedure.

Key words

total synthesis - rosuvastatin calcium - Wittig olefination - lactone reduction - diastereoselective reduction - sugar chemistry - d-glucose

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