Liebigs Annalen der Chemie

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

S Marczak, M Masnyk, J Wicha

文献索引：Marczak, Stanislaw; Masnyk, Marek; Wicha, Jerzy Liebigs Annalen der Chemie, 1990 , # 4 p. 345 - 347

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被引用次数: 5

摘要

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.