Total Synthesis of Brevenal
Total Synthesis of Brevenal
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DOI：
10.1021/ol900769d
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发表时间：
2009-06-18
期刊：
影响因子：
5.2
通讯作者：
Yamamoto, Yoshinori
中科院分区：
文献类型：
--
作者：
Takamura, Hiroyoshi;Kikuchi, Shigetoshi;Yamamoto, Yoshinori
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。
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.