A convergent synthesis of (+)-pancratistatin based on intramolecular electrophilic aromatic substitution
A convergent synthesis of (+)-pancratistatin based on intramolecular electrophilic aromatic substitution
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DOI：
10.1016/s0040-4020(97)00373-6
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发表时间：
1997-08-11
期刊：
影响因子：
2.1
通讯作者：
Haseltine, J
中科院分区：
文献类型：
--
作者：
Doyle, TJ;Hendrix, M;Haseltine, J
本文报道了（+）-潘曲他汀（1）的收敛式合成。具体地，胡椒基溴和丙酮化的conduritol A的光学活性加合物被转化为来自1的Danishefsky-Lee合成的酯化阶段中间体。通过胡椒基化conduritol内的分子内亲电芳香取代建立碳骨架。在此操作中观察到一些竞争性阳离子重排，取决于胡椒基结构域中的2-取代基有利于攻击胡椒基苄基碳的程度。(C)1997 Elsevier Science Ltd.
A convergent formal synthesis of (+)-pancratistatin (1) is reported. Specifically, an optically active adduct of piperonyl bromide and acetonated conduritol A was converted to a]ate-stage intermediate from the Danishefsky-Lee synthesis of 1. The carbon skeleton was established via intramolecular electrophilic aromatic substitution within the piperonylated conduritol. Some competitive cationic rearrangement was observed in this operation, being dependent on the degree to which a 2-substituent in the piperonyl domain favors attack ipso to the piperonyl benzylic carbon. (C) 1997 Elsevier Science Ltd.