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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

✍ Scribed by Mori, Kenji ;Takikawa, Hirosato ;Nishimura, Yutaka ;Horikiri, Hiromasa

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
687 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

(–)‐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.

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## Abstract Both (1__R__)‐ and (1__S__)‐hydroxy derivatives of (+)‐exo‐brevicomin {(1__R__,1′__R__,5′__R__,7′__R__)‐1‐(5′‐methyl‐6′,8′‐dioxabicyclo[3.2.1]‐octyl)ethanol (1) and its (1__S__)‐isomer (2)} were synthesized by employing Sharpless asymmetric dihydroxylation as the key reaction.