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Pheromone Synthesis, CXLII. A New Synthesis of (3S,4R)-8-Nonene-3,4-diol, the Key Intermediate for the Synthesis of (+)-endo-Brevicomin

✍ Scribed by Mori, Kenji ;Kiyota, Hiromasa


Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
363 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis


Abstract

(3__S__,4__R__)‐8‐Nonene‐3,4‐diol (2), the key intermediate for the synthesis of the bark beetle pheromone (+)‐endo‐brevicomin (1), has been synthesized in 46% overall yield (10 steps) based on erythritol (6) by employing lipase‐mediated asymmetric acetylation as one of the steps.


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Pheromone synthesis, CLXX. A new synthes
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## Abstract Faranal (1), the trail‐following pheromone of the worker of Pharaoh's ant (__Monomorium pharaonis__), was synthesized by the coupling reaction of the iododiene 3 with the chiral building block 8 as the key step. The geometrically pure iododiene 3 was prepared by the zirconocene‐mediated