通过手性有机锂化合物的不对称取代实现双苄基异喹啉生物碱小檗胺的形式合成。
Formal synthesis of the bisbenzylisoquinoline alkaloid berbamunine by asymmetric substitution of chiral organolithium compounds.
作者信息
Gawley Robert E, Smith Gregory A
机构信息
Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701, U.S.A.
出版信息
ARKIVOC. 2011 Jan 30;2011(Pt 5):167-179.
Abstract
Asymmetric alkylation of enantiomeric tetrahydroisoquinolyl oxazolines was achieved with 96-97% diastereoselectivity. Removal of the oxazoline chiral auxiliary and further transformations provide a straightforward synthesis of the two synthetic intermediates that were previously synthesized by resolution, and which comprise a formal synthesis of berbamunine by Ullman coupling.
摘要
对映体四氢异喹啉基恶唑啉的不对称烷基化反应以96 - 97%的非对映选择性实现。恶唑啉手性辅助基团的去除及进一步转化提供了两种合成中间体的直接合成方法，这两种中间体此前是通过拆分合成的，且通过乌尔曼偶联构成了小檗胺的形式合成。
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