Biomimetic total synthesis of gambogin and rate acceleration of pericyclic reactions in aqueous media

被引：69

作者：

Nicolaou, KC

Xu, H

Wartmann, M

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[3] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 05期

关键词：

Claisen rearrangement; Diels-Alder reaction; natural products; rate acceleration; total synthesis;

D O I：

10.1002/anie.200462211

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A significant rate acceleration of a Claisen rearrangement and of a Claisen/Diels-Alder reaction cascade sequence was observed in the presence of water. This reaction sequence was used in a total synthesis of gambogin (1) from a tricyclic dialkene 3 via 2.

引用

页码：756 / 761

页数：6

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[1] STERIC AND ELECTRONIC FACTORS WHICH EFFECT THERMAL CYCLIZATION OF META-SUBSTITUTED ARYL PROPARGYL ETHERS - SYNTHESIS OF 5-SUBSTITUTED AND 7-SUBSTITUTED 3-CHROMENES [J].