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Synthesis of Posticlure [(6 Z ,9 Z ,11 S ,12 S )‐11,12‐Epoxyhenicosa‐6,9‐diene], the Female Sex Pheromone of Orgyia postica
Author(s) -
Muto Shinetsu,
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)2001:24<4635::aid-ejoc4635>3.0.co;2-j
Subject(s) - diene , sharpless asymmetric dihydroxylation , sex pheromone , chemistry , stereochemistry , dihydroxylation , enantioselective synthesis , botany , organic chemistry , biology , catalysis , natural rubber
Starting from commercially available ( E )‐2‐dodecenoic acid, posticlure [(6 Z ,9 Z ,11 S ,12 S )‐11,12‐epoxyhenicosa‐6,9‐diene ( 1 )], the female sex pheromone of the tussock moth ( Orgyia postica ), was synthesized in 25% overall yield (6 steps) by employing Sharpless asymmetric dihydroxylation as the key step. Its (11 R ,12 R )‐isomer as well as its racemate were also synthesized.