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通过卡宾环化-环加成串联策略对(-)-印度马钱子碱进行不对称全合成。

Asymmetric total synthesis of (-)-indicol by a carbene cyclization-cycloaddition cascade strategy.

作者信息

Lam Sze Kui, Chiu Pauline

机构信息

Department of Chemistry, and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, University of Hong Kong, Pokfulam Road, Hong Kong, PR China.

出版信息

Chemistry. 2007;13(34):9589-99. doi: 10.1002/chem.200700838.

Abstract

The first total synthesis of a secodolastane, (-)-indicol, has been accomplished. The key reaction is a rhodium(II)-mediated carbene cyclization-cycloaddition cascade, by which the core bicyclo[5.4.0]undecane skeleton was assembled. In this one-pot reaction, a domino series of transformations resulting in the construction of three sigma bonds and three stereocenters was realized in good yield.

摘要

首次完成了倍半朵拉烷(-)-印度醇的全合成。关键反应是铑(II)介导的卡宾环化-环加成串联反应,通过该反应构建了核心双环[5.4.0]十一烷骨架。在这个一锅反应中,以良好的产率实现了一系列多米诺式转化,形成了三个σ键和三个立体中心。

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