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一种基于爱尔兰-克莱森重排和关环复分解反应的稠合环醚合成新变体。

A new variant of fused cyclic ether synthesis based on Ireland-Claisen rearrangement and RCM.

作者信息

Domon Daisuke, Fujiwara Kenshu, Kawamura Natsumi, Katoono Ryo, Kawai Hidetoshi, Suzuki Takanori

机构信息

Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 606-0810, Japan.

出版信息

Nat Prod Commun. 2013 Jul;8(7):929-34.

Abstract

A new variant of fused cyclic ether synthesis based on Ireland-Claisen rearrangement and ring-closing olefin metathesis (RCM) was developed. The Ireland-Claisen rearrangement of a (Z)-3-alkoxyprop-2-en-1-yl glycolate ester having a cyclic ether on the oxygen at C3 of the (Z)-prop-2-en-1-yl group stereoselectively produced an anti-alpha,beta-dialkoxyester, which was successfully transformed to a fused bicyclic ether via a reaction sequence including RCM.

摘要

基于爱尔兰-克莱森重排和闭环烯烃复分解反应(RCM),开发了一种新型稠合环醚合成方法。在(Z)-烯丙基的C3位氧原子上带有环醚的(Z)-3-烷氧基丙-2-烯-1-基乙醇酸酯的爱尔兰-克莱森重排反应立体选择性地生成了反式α,β-二烷氧基酯,该产物通过包括RCM在内的反应序列成功转化为稠合双环醚。

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