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Studies on the identification and synthesis of insect pheromone: XVI. Synthesis of the optically active sex pheromone of gypsy moth and its three other optical isomers
Author(s) -
GuoQiang Lin,
BiChi Wu,
LinYu Liu,
XianQin Wang,
WeiShan Zhou
Publication year - 1984
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19840020113
Subject(s) - chemistry , pheromone , gypsy moth , sex pheromone , optically active , stereochemistry , yield (engineering) , insect , organic chemistry , botany , lepidoptera genitalia , biology , materials science , metallurgy
The sex pheromone of gypsy moth (+)‐(7 R , 8S)‐7,8‐epoxy‐2‐methyl‐octadecane (la) and its three other optical isomers lb—d were synthesized stereoselectively from (+)‐( R )‐glyceraldehyde acetonide (2), obtained from (+)‐mannitol, in 9—10 steps in an overall yield of 20—30%.