Total Synthesis of seco-Plakortolide E and (-)-ent-Plakortolide I: Absolute Configurational Revision of Natural Plakortolide I
Total Synthesis of seco-Plakortolide E and (-)-ent-Plakortolide I: Absolute Configurational Revision of Natural Plakortolide I
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DOI：
10.1021/ol203185f
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发表时间：
2012-01-20
期刊：
影响因子：
5.2
通讯作者：
Vatele, Jean-Michel
中科院分区：
文献类型：
--
作者：
Barnych, Bogdan;Vatele, Jean-Michel
从（S）-2-甲基缩水甘油完成了（-）-对映-plakortolide I和开环-plakortolide E的首次全合成。相关的关键反应涉及非对映选择性Mukaiyama羟醛缩合反应，区域选择性氢过氧硅烷化，和1，2-二氧杂环己烷环的分子内迈克尔加成的氢过氧化物基团的丁烯二醇的阐述。该合成方法修正了plakortolide I的绝对构型，并修正了plakortolide E的结构。
A first total synthesis of (-)-ent-plakortolide I and seco-plakortolide E was accomplished from (S)-2-methylglycidol. The relevant key reactions involve a diastereoselective Mukaiyama aldol reaction, a regioselective hydroperoxysilylation, and elaboration of the 1,2-dioxane ring by intramolecular Michael addition of a hydroperoxide group to a butenolide. This synthesis allowed the revision of the absolute configuration of plakortolide I and structural revision of plakortolide E.