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Synthesis of (1 R *,3 R *,7 R *)‐3‐Methyl‐α‐himachalene, the Racemate of the Male‐Produced Sex Pheromone of the Sandfly Lutzomyia longipalpis from Jacobina, Brazil
Author(s) -
Sano Satoshi,
Mori Kenji
Publication year - 1999
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/(sici)1099-0690(199907)1999:7<1679::aid-ejoc1679>3.0.co;2-o
Subject(s) - sex pheromone , pheromone , chemistry , stereochemistry , sandfly , intramolecular force , botany , biology , leishmania , parasite hosting , world wide web , computer science
Four stereoisomers ( 1a–d ) of (±)‐3‐methyl‐α‐himachalene were synthesized by employing the intramolecular Diels–Alder reaction of (±)‐ 14 to (±)‐ 18 as the key‐step. The male‐produced sex pheromone of the sandfly Lutzomyia longipalpis was shown to possess the structure and relative configuration as depicted in 1c .