Catalyzed asymmetric Diels-Alder reaction of benzoquinone. Total synthesis of (-)-ibogamine

被引：69

作者：

White, JD ^{[1
]}

Choi, YG ^{[1
]}

机构：

[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 15期

关键词：

D O I：

10.1021/ol0001463

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The Diets-Alder addition of diene 2 with benzoquinone catalyzed by (S)-BINOL-TiCl2 produced cycloadduct 5 in >65% yield and 87% ee. The cycloadduct was transformed into (-)-ibogamine in nine steps (10% overall yield from benzoquinone). A model for the transition state leading to 5 is proposed.

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页码：2373 / 2376

页数：4

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