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A Facile Asymmetric Synthesis of the Compactin Lactone Moiety

✍ Scribed by Schabbert, Silke ;Tiedemann, Ralf ;Schaumann, Ernst

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 227 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719970514

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✦ Synopsis

Abstract

Starting from (R)‐O‐benzylglycidol and a sulfur‐stabilized allyl anion, a (3 + 3) synthesis of the α,β‐unsaturated (6__S__)‐δ‐lactone 7 is achieved. Subsequent diastereoselective addition of a phenyldimethylsilyl cuprate and unmasking of the latent hydroxy function provides the lactone unit of compactin.

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