Direct stereocontrolled synthesis of polyoxygenated hydrobenzofurans and hydrobenzopyrans from p-peroxy quinols
Direct stereocontrolled synthesis of polyoxygenated hydrobenzofurans and hydrobenzopyrans from p-peroxy quinols
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DOI：
10.1021/ol702236e
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发表时间：
2007-11-22
期刊：
影响因子：
5.2
通讯作者：
Urbano, Antonio
中科院分区：
文献类型：
--
作者：
Barradas, Silvia;Carmen Carreno, M.;Urbano, Antonio
采用酸碱串联催化法，对C-4羟基烷基链的对过氧喹啉进行了一锅法合成了氢苯并呋喃和氢苯并吡喃三环环氧化合物。在这种转变中，以高度立体控制的方式创造了两个新的循环和四个新的立体中心。该策略的有效性通过天然产物Cleroindicin D的首次全合成和结构修正得到说明。
An acidic-basic tandem catalytic process on p-peroxy quinols with hydroxy alkyl chains at C-4 allowed the one-pot synthesis of hydrobenzofuran and hydrobenzopyran tricyclic epoxides. In this transformation, two new cycles and four new stereogenic centers are created in a highly stereocontrolled manner. The usefulness of the strategy is illustrated with the first total synthesis and structural revision of natural product Cleroindicin D.