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Synthesis of (+)-disparlure using the reaction of 6-methylheptyl phenyl sulfone with trimethylsilyloxirane and asymmetric epoxidation

✍ Scribed by Marczak, Stanislaw ;Masnyk, Marek ;Wicha, Jerzy

Publisher: John Wiley and Sons
Year: 1990
Tongue: English
Weight: 305 KB
Volume: 1990
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199019900165

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✦ Synopsis

Abstract

Reaction of lithiated sulfone 3 with trimethyl(oxiranyl)silane 4, followed by acid hydrolysis, afforded the (Z)‐allylic alcohol 6 contaminated with its (E) isomer. Epoxidation of 6 by the Sharpless procedure yielded the hydroxy epoxide, which was isolated as its enantiomerically pure 3,5‐dinitrobenzoyl derivative 7 and transformed into (+)‐disparlure 1 via alcohol 8 and tosylate 9.

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