Synthesis of the Acyclic Carbon Skeleton of Filipin III
Synthesis of the Acyclic Carbon Skeleton of Filipin III
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DOI：
10.1021/acs.joc.6b01166
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发表时间：
2016-09-16
影响因子：
3.6
通讯作者：
Cossy, Janine
中科院分区：
文献类型：
--
作者：
Brun, Elodie;Bellosta, Veronique;Cossy, Janine
filipin III 是一种具有 11 个立构中心的多烯大环内酯，其碳骨架的合成是使用从己醛开始的 19 个步骤的最长线性序列的收敛策略实现的。使用两个连续的 Heck 耦合作为关键步骤实现了多烯的构建。通过利用埃文斯醛醇化、1,3-顺式醛醇化、对映选择性和非对映选择性烯丙基化、半缩醛化/oxa-Michael序列和1,3-顺式还原来控制多元醇片段的立体中心。使用 1,5-抗非对映选择性醛醇缩合，然后进行 1,3-抗还原，将多元醇和多烯片段偶联。
The synthesis of the carbon skeleton of filipin III, a polyenic macrolactone possessing 11 stereogenic centers, was achieved using a convergent strategy with the longest linear sequence of 19 steps starting from hexanal. Construction of the polyene was realized using two successive Heck couplings as the key steps. Control of the stereogenic centers of the polyol fragment was performed by utilizing an Evans aldolization, a 1,3-syn aldolization, enantio-and diastereoselective allylations, a hemiacetalization/oxa-Michael sequence, and a 1,3-syn reduction. The polyol and polyenic fragments were coupled using a 1,5-anti diastereoselective aldolization followed by a 1,3-anti reduction.