Intramolecular Condensation via an o-Quinone Methide: Total Synthesis of (±)-Heliol

被引：36

作者：

Green, Jason C. ^{[1
]}

Brown, Eric R. ^{[1
]}

Pettus, Thomas R. R. ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 12期

基金：

美国国家科学基金会;

关键词：

MARINE SPONGE; SESQUITERPENE; (+)-CURCUPHENOL; HELIANANE;

D O I：

10.1021/ol301092w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An acid-catalyzed intramolecular [4 + 2] cycloaddition of a non-natural bisabolene is reported. The key cyclocondensation was developed to access cyclic sesquiterpenes from linear phenolic precursors by generating a reactive o-quinone methide intermediate to initiate a cascade reaction. The new method was applied to the first total synthesis of (+/-)-heliol.

引用

页码：2929 / 2931

页数：3

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