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Synthesis of (1 R ,4 R ,5 S )‐(+)‐Acoradiene, the Structure Proposed for the Aggregation Pheromone of the Broad‐Horned Flour Beetle
Author(s) -
Kurosawa Satoshi,
Bando Masahiko,
Mori Kenji
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200112)2001:23<4395::aid-ejoc4395>3.0.co;2-q
Subject(s) - pheromone , chemistry , stereochemistry , pulegone , olefin metathesis , metathesis , botany , organic chemistry , biology , food science , essential oil , polymerization , polymer
(1 R ,4 R ,5 S )‐(+)‐Acoradiene {1,8‐dimethyl‐4‐(1′‐methylethenyl)spiro[4.5]dec‐7‐ene ( 1 )}, the structure proposed for the aggregation pheromone of the broad‐horned flour beetle ( Gnatocerus cornutus ), was synthesized from ( R )‐(+)‐pulegone ( 2 ) by employing the ring‐closing olefin metathesis of diene 9 as the key step, and confirming the structure of intermediate 11 by X‐ray analysis. The spectral properties of (+)‐ 1 were different from those reported for the pheromone, whose proposed structure 1 was therefore proven incorrect.