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Synthesis of Tribolure, the Common Aggregation Pheromone of Four Tribolium Flour Beetles
Author(s) -
Wang Chao,
He Chengyu,
Shi Yong,
Xiang Hua,
Tian Weisheng
Publication year - 2015
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.201500334
Subject(s) - chemistry , pheromone , stereocenter , sapogenin , stereochemistry , organic chemistry , botany , enantioselective synthesis , catalysis , medicine , alternative medicine , pathology , biology
Abstract Herein we report a synthesis of the natural tribolure, an aggregation pheromone which consists of (4 R ,8 S )‐, (4 R ,8 R )‐, (4 S ,8 S )‐, and (4 S ,8 R )‐4,8‐dimethyldecanals in a ratio of 4/4/1/1, from ( R )‐4‐methyl‐ δ ‐valerolactone, a byproduct of the degradation of steroidal sapogenins. Merging the stereoisomers of the same ratios into one synthetic target and using the same chiron for the construction of the C4 stereocenters are notable features of this synthesis.