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
收藏
页码：6304 / 6307
页数：4
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