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Synthesis 2012; 44(11): 1700-1710
DOI: 10.1055/s-0031-1290916
DOI: 10.1055/s-0031-1290916
paper
The Use of a Lactonized Statin Side-Chain Precursor in a Concise and Efficient Assembly of Pitavastatin
Further Information
Publication History
Received: 16 February 2012
Accepted after revision: 09 March 2012
Publication Date:
26 April 2012 (online)
Abstract
A concise and simple synthetic route to pitavastatin is described. The approach involves a highly stereoselective Wittig olefination reaction between a lactonized statin side-chain precursor and the triphenylphosphonium bromide salt of the corresponding quinoline heterocyclic core. The necessary O-tert-butyl(dimethyl)silyl-protected pitavastatin lactone was obtained in 75% yield and high purity by simple crystallization from aqueous methanol. Subsequent deprotection, hydrolysis, and cation exchange in a one-pot operation provided pitavastatin calcium in 93% yield.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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