Total Synthesis of Brevenal

A total synthesis of brevenal is described. The pentacyclic ether core was constructed by the intramolecular allylation of alpha-acetoxy ether and subsequent ring-closing metathesis. Both of the diene side chains were introduced by Wittig olefination and a Horner-Wadsworth-Emmons reaction, respectively, in a highly stereoselective manner.

描述了一种短裸甲藻毒素（brevenal）的全合成。五环醚核心是通过α-乙酰氧基醚的分子内烯丙基化以及随后的闭环复分解反应构建的。两条二烯侧链分别通过维蒂希烯化反应和霍纳尔 - 沃兹沃思 - 埃蒙斯反应以高度立体选择性的方式引入。