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Pheromone Synthesis, CXLIX. Synthesis of (2 E ,4 E ,6 R ,10 S )‐4,6,10‐Trimethyl‐2,4‐dodecadien‐7‐one – the Major Component of the Sex Pheromone of the Maritime Pine Scale ( Matsucoccus feytaudi ) – and its Three Stereoisomers
Author(s) -
Mori Kenji,
Harashima Susumu
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199319930165
Subject(s) - chemistry , pheromone , stereochemistry , citronellol , cleavage (geology) , ring (chemistry) , organic chemistry , botany , geraniol , chromatography , fracture (geology) , essential oil , biology , geotechnical engineering , engineering
(2 E ,4 E ,6 R ,10 S )‐4,6,10‐Trimethyl‐2,4‐dodecadien‐7‐one ( 1 ) – the major component of the sex pheromone of the maritime pine scale – and its three stereoisomers were synthesized by starting from ( R )‐ or ( S )‐citronellol ( 4 ) and employing the asymmetric epoxidation ( 9 → 10 ) and the palladium‐catalyzed reductive cleavage of the epoxy ring ( 13 → 14 ) as the key steps.