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Pheromone Synthesis, CLXXVIII . – Synthesis of (−)‐ exo ‐Isobrevicomin and Its (−)‐ endo Isomer, the Components of The Male‐Produced Volatiles of the Mountain Pine Beetle, Dendroctonus ponderosae
Author(s) -
Mori Kenji,
Takikawa Hirosato,
Nishimura Yutaka,
Horikiri Hiromasa
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970209
Subject(s) - chemistry , dihydroxylation , dendroctonus , mountain pine beetle , octane , sharpless asymmetric dihydroxylation , stereochemistry , acetal , pheromone , terpene , enantioselective synthesis , bark beetle , organic chemistry , catalysis , twig , botany , geography , forestry , biology
(–)‐ exo ‐Isobrevicomin {(1 S ,5 R ,7 S )‐(–)‐5‐ethyl‐7‐methyl‐6,8‐dioxabicyclo[3.2.1]octane ( 1 )} and its (–)‐ endo isomer [(1 S ,5 R ,7 R )‐ 2 ] were synthesized by employing the acetylenic acetal 7 as the common intermediate and by using the Sharpless asymmetric dihydroxylation and lipase‐catalyzed acetylation as the key reactions.