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Synthesis 2016; 48(23): 4167-4174
DOI: 10.1055/s-0035-1562787
DOI: 10.1055/s-0035-1562787
paper
An Asymmetric Synthesis of Rosuvastatin Calcium
Further Information
Publication History
Received: 15 April 2016
Accepted after revision: 20 June 2016
Publication Date:
16 August 2016 (online)
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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-glucoseSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562787.
- Supporting Information
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