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

Marczak Stanislaw | Zendy; Masnyk Marek | Zendy; Wicha Jerzy | Zendy

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

Author(s) -

Marczak Stanislaw,

Masnyk Marek,

Wicha Jerzy

Publication year - 1990

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.199019900165

Subject(s) - chemistry , sulfone , epoxide , alcohol , silane , hydrolysis , derivative (finance) , allylic rearrangement , organic chemistry , allylic alcohol , catalysis , financial economics , economics

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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