Stereoselective total synthesis and stereochemistry confirmation of photo-mycolactones
作者:Xiaoyong Li、Vaddela Sudheer Babu、Yoshito Kishi
DOI:10.1016/j.tetlet.2014.12.024
日期:2015.6
With use of the LiTMP-induced Hodgson cyclopropanation of an epoxide-olefin to a bicyclo[3.1.0]hexanol as the key step, a stereoselective total synthesis of photo-mycolactones was achieved. Each of the four diastereomeric epoxide-olefins, selectively prepared from (R)- and (S)-glycidols, yielded the corresponding unique bicyclo[3.1.0]hexanol. Four bicyclo[3.1.0]hexanols 16, dia-16, 19, and dia-19 were
使用LiTMP诱导的环氧烯烃至双环[3.1.0]己醇的霍奇森环丙烷化作为关键步骤,实现了光-甲基内酯的立体选择性全合成。由(R)-和(S)-糖醇选择性地制备的四种非对映体环氧烯烃中的每一种,产生相应的独特的双环[3.1.0]己醇。四双环[3.1.0]己醇16,直径- 16,19,和直径- 19转化成四伯醇17,直径- 17,20,和直径- 20,是以前关于光-内酯的研究中使用的中间体。该合成证实了先前提出的用于光-甲基内酯的立体化学。