New Route to the Ergoline Skeleton via Cyclization of 4-Unsubstituted Indoles

被引：10

作者：

Burley, Scott D. ^{[1
]}

Lam, Vicky V. ^{[2
]}

Lakner, Frederick J. ^{[2
]}

Bergdahl, B. Mikael ^{[1
]}

Parker, Matthew A. ^{[1
]}

机构：

[1] San Diego State Univ, Dept Chem, San Diego, CA 92182 USA

[2] ChemDiv Inc, San Diego, CA 92121 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 11期

基金：

美国国家卫生研究院;

关键词：

LYSERGIC-ACID; (+)-LYSERGIC ACID; ERGOT ALKALOIDS; CHLORIDE;

D O I：

10.1021/ol400620a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new route to the ergoline skeleton has been developed that does not require prior functionalization of the indole 4-position. The indole nucleus is introduced late in the synthesis to allow for eventual efficient introduction of substituents in this region. Key steps include Negishi coupling of a three-carbon chain to a bromonicotinate ester, Fischer indole synthesis to facilitate incorporation of substituents via phenylhydrazines, and Pd-catalyzed cyclization to form the ergoline C ring.

引用

页码：2598 / 2600

页数：3

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