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

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...

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Bibliographic Details
Published in:	Organic letters Vol. 15; no. 11; pp. 2598 - 2600
Main Authors:	Burley, Scott D, Lam, Vicky V, Lakner, Frederick J, Bergdahl, B. Mikael, Parker, Matthew A
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 07-06-2013
Subjects:	Catalysis Cyclization Ergolines - chemical synthesis Ergolines - chemistry Indoles - chemistry Molecular Structure Niacin - chemistry Palladium - chemistry Phenylhydrazines - chemistry
Online Access:	Get full text
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Summary:	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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol400620a