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Conversion of pravastatin into an advanced intermediate for the synthesis of the HMG-CoA reductase inhibitor BB-476

✍ Scribed by J.J. Cronje Grove; Pieter S. van Heerden; Daneel Ferreira; Barend C.B. Bezuidenhoudt

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 308 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.10.080

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✦ Synopsis

Rearrangement of the decalin system of pravastatin under S N 2 0 Mitsunobu conditions and subsequent selective hydrolysis and oxidation afforded a key dienone 23, which upon copper-catalyzed addition of a 1E-propenyl moiety established the carbon framework of BB-476 3 in high diastereomeric excess.

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