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A New and Efficient Synthesis of the HMG-CoA Reductase Inhibitor Pitavastatin

✍ Scribed by Murat Acemoglu; Andre Brodbeck; Angel Garcia; Dominique Grimler; Marc Hassel; Bernhard Riss; Robert Schreiber

Publisher: John Wiley and Sons
Year: 2007
Tongue: German
Weight: 147 KB
Volume: 90
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200790106

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✦ Synopsis

Abstract

A new synthetic method for the preparation of pitavastatin is described. The approach circumvents various synthetic problems associated with the buildup of the 3,5‐dihydroxy‐C~7~ acid side chain of HMG‐CoA reductase inhibitors (statins). The use of the C~6~‐amide derivative 5 instead of ester derivatives in the coupling reaction with carboxaldehyde 8 (Scheme 3) prevents undesired side reactions, such as eliminations and retro‐aldol reactions. The method provides synthetic statins, such as pitavastatin, in >99% ee and exceptionally high overall yield. The enantiomerically pure starting material, (3__S__)‐3‐{[(tert‐butyl)dimethylsilyl]oxy}‐5‐oxo‐5‐{[(1__S__)‐1‐phenylethyl]amino}pentanoic acid (3c), is prepared by an improved procedure from 3‐{[(tert‐butyl)dimethylsilyl]oxy}glutaric anhydride (1) and (1__S__)‐1‐phenylethylamine (2c; Scheme 1).

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