An Allenic Pauson-Khand Approach to 6,12-Guaianolides

被引：31

作者：

Grillet, Francois ^{[1
]}

Huang, Chaofeng ^{[1
]}

Brummond, Kay M. ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 23期

基金：

美国国家卫生研究院;

关键词：

ACID-CATALYZED ALLYLBORATION; NUCLEOPHILIC-ADDITION; GUAIANOLIDES; LACTONES; THAPSIGARGINS; INHIBITORS; ALDEHYDES; REAGENTS; CYCLIZATION; DISCOVERY;

D O I：

10.1021/ol2028515

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclocarbonylation of alpha-methylene butyrolactone-containing allene-ynes affords 6,12-guaianolide ring systems. Incorporation of the a-methylene butyrolactone early in a synthetic sequence is rare for reactivity reasons; however, this moiety proves to be beneficial to the allenic Pauson-Khand reaction. The three double bonds and the ketone in the resulting 5-7-5 ring system bear significant differences in their reactivity and are ideally positioned for synthetic application to 6,12-guaianolides and analogs.

引用

页码：6304 / 6307

页数：4

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