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Asymmetric Synthesis of Both Enantiomers of Disparlure
Author(s) -
Wang Zhigang,
Zheng Jianfeng,
Huang Peiqiang
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201100482
Subject(s) - chemistry , enantiomer , sex pheromone , sharpless epoxidation , enantioselective synthesis , propargyl alcohol , pheromone , stereochemistry , alcohol , total synthesis , sharpless asymmetric dihydroxylation , organic chemistry , zoology , botany , catalysis , biology
Starting from propargyl alcohol ( 12 ), and on the basis of Zhou's modified Sharpless asymmetric epoxidation, the sex pheromone of the Gypsy moth, disparlure (+)‐ 8 and its enantiomer (−)‐ 8 have been synthesized, each in six steps, with overall yields of 29% for (+)‐ 8 and 27% for (−)‐ 8 ( ee >98%). The use of the sequential coupling tactic renders the method flexible, which is applicable to the synthesis of other cis ‐epoxy pheromones.