دورية أكاديمية

Stereospecific synthesis of S-(−)-trans-verbenol and its antipode by inversion of sterically hindered alcohols.

التفاصيل البيبلوغرافية
العنوان: Stereospecific synthesis of S-(−)-trans-verbenol and its antipode by inversion of sterically hindered alcohols.
المؤلفون: Liu, Fu, Fang, Jia-Xing, Kong, Xiang-Bo, Zhang, Su-Fang, Zhang, Zhen
المصدر: Journal of Asian Natural Products Research; Jun2022, Vol. 24 Issue 6, p569-576, 8p
مصطلحات موضوعية: ORGANIC compound analysis, EXPERIMENTAL design, MASS spectrometry, RESEARCH funding, ALCOHOLS (Chemical class), MOLECULAR structure, CHROMATOGRAPHIC analysis
مستخلص: 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 SN2 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. [ABSTRACT FROM AUTHOR]
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قاعدة البيانات: Complementary Index
الوصف
تدمد:10286020
DOI:10.1080/10286020.2020.1839433