Facile asymmetric construction of a functionalized dodecahydrobenz[a]indolo[3,2-h]quinolizine template
Facile asymmetric construction of a functionalized dodecahydrobenz[a]indolo[3,2-h]quinolizine template
复制标题
DOI：
10.1016/j.tet.2009.09.097
复制
发表时间：
2009-12-05
期刊：
影响因子：
2.1
通讯作者：
Saha, Basu
中科院分区：
文献类型：
--
作者：
Allin, Steven M.;Duffy, Liam J.;Saha, Basu
我们报道了一种高度非对映选择性的方法，用于合成功能化的十二氢苯并[a]吲哚并[3，2-h]喹嗪环系统，该系统作为manadomanzamine生物碱的杂环核心存在。我们已经实现了完全控制的相对和绝对的立体化学在三个连续的立体中心在环位置1，10和24在只有两个线性合成步骤。将有用的官能团引入杂环骨架是重要的，因为这可以允许将来的衍生化，以及该路线在manadomanzamine天然产物的不对称合成中的应用。(C)2009爱思唯尔有限公司保留所有权利。
We report a highly diastereoselective approach for the synthesis of a functionalized dodecahydrobenz[a]indolo[3,2-h]quinolizine ring system that is present as the heterocyclic core of the manadomanzamine alkaloids. We have achieved complete control over the relative and absolute stereochemistries at the three contiguous stereocentres at ring positions 1, 10 and 24 in only two linear synthetic steps. The introduction of useful functionality to the heterocyclic skeleton is significant as this may allow for future derivatization, and application of this route in an asymmetric synthesis of the manadomanzamine natural products. (C) 2009 Elsevier Ltd. All rights reserved.