Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction
Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction
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DOI：
10.1021/ol202966m
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发表时间：
2012-01-06
期刊：
影响因子：
5.2
通讯作者：
Sammakia, Tarek
中科院分区：
文献类型：
--
作者：
Gazaille, Jeffrey A.;Abramite, Joseph A.;Sammakia, Tarek
本文介绍了利用分子内乙烯基羟醛缩合反应制备一种用于合成佩兰苷A的高级中间体。该反应应用于化合物19，并以高产率和良好的非对映选择性水平进行。将Achmatowicz反应应用于该中间体提供了相应的吡喃酮，这是一种适合转化为天然产物的后期中间体。
The use of the intramolecular vinylogous aldol reaction for the preparation of an advanced intermediate for the synthesis of peloruside A Is described. The reaction was applied to compound 19 and proceeds in high yield and good levels of diastereoselectivity. Application of the Achmatowicz reaction to this intermediate provided the corresponding pyranone, a late stage intermediate well positioned for conversion to the natural product.