快速构建 daphniphyllum 生物碱 daphnilongeranin B 和 daphniyunnine D 的[7-5-5]全碳三环核心。

Expedient construction of the [7-5-5] all-carbon tricyclic core of the Daphniphyllum alkaloids daphnilongeranin B and daphniyunnine D.

机构信息

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.

出版信息

Org Lett. 2012 Apr 6;14(7):1684-7. doi: 10.1021/ol3002267. Epub 2012 Mar 9.

Abstract

A synthetic strategy for the construction of the [7-5-5] all-carbon tricyclic core of numerous calyciphylline A-type Daphniphyllum alkaloids has been developed using a key intramolecular Pauson-Khand reaction. A subsequent base-mediated double-bond migration and a regio- and stereoselective radical late stage allylic oxygenation provide access to the substitution patterns of daphnilongeranin B and daphniyunnine D.

摘要

一种构建众多 calyciphylline A 型 Daphniphyllum 生物碱[7-5-5]全碳三环核心的综合策略已经开发出来，使用了关键的分子内 Pauson-Khand 反应。随后的碱介导的双键迁移和区域和立体选择性自由基晚期烯丙基氧合提供了 daphnilongeranin B 和 daphniyunnine D 的取代模式。