Abstract

S-(−)-trans-Verbenol (1) and its antipode, R-(+)-trans-verbenol (1′) have been confirmed as the critical pheromone components of bark beetles. Synthesis of these two active secondary alcohols (1 and 1′) from commercially available starting materials S-α-pinene and R-α-pinene was reported. The key steps were mainly depended on the effective S_N2 stereo-inversion of the hydroxy group of sterically hindered alcohols (3 and 3′), using Mitsunobu reaction or hydrolysis of mesylate ester, alternatively. Our results provide a new and stereo-selectivity way to obtain optically active insect pheromones.

中文翻译：

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空间位阻醇倒置立体特异性合成S-(-)-trans-verbenol及其对映体

摘要

S -(-)- trans -Verbenol ( 1 ) 及其对映体R -(+)- trans -verbenol ( 1' ) 已被证实是树皮甲虫的关键信息素成分。报道了由市售起始原料S - α -蒎烯和R - α - 蒎烯合成这两种活性仲醇（1和1' ）。关键步骤主要取决于空间位阻醇（ 3和3）羟基的有效S _{N 2 立体反转。}')，或者使用Mitsunobu反应或甲磺酸酯的水解。我们的结果为获得光学活性昆虫信息素提供了一种新的立体选择性方法。