Direct, Chemoselective N-tert-Prenylation of Indoles by C----H Functionalization

Four steps in one: The direct prenylation of indoles at N‐1 can be achieved by CH functionalization in the presence of a PdII source. This reaction proceeds by direct intermolecular olefin amination, tolerates a broad range of functional groups, and can be carried out on a gram scale, as demonstrat...

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Bibliographic Details
Published in:	Angewandte Chemie (International ed.) Vol. 48; no. 38; pp. 7025 - 7029
Main Authors:	Luzung, Michael R, Lewis, Chad A, Baran, Phil S
Format:	Journal Article
Language:	English
Published:	Weinheim Wiley-VCH Verlag 01-01-2009 WILEY‐VCH Verlag
Subjects:	CH functionalization Hydrogen Bonding Indole Alkaloids - chemical synthesis Indole Alkaloids - chemistry indoles Prenylation synthetic methods
Online Access:	Get full text
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Summary:	Four steps in one: The direct prenylation of indoles at N‐1 can be achieved by CH functionalization in the presence of a PdII source. This reaction proceeds by direct intermolecular olefin amination, tolerates a broad range of functional groups, and can be carried out on a gram scale, as demonstrated by the formal syntheses of a number of natural products and the synthesis of an antifungal natural product (see scheme).
Bibliography:	http://dx.doi.org/10.1002/anie.200902761 We are grateful to Dr. Benjamin Hafensteiner, Dr. Carlos Guerrero, and Dr. Narendra Ambhaikar for preliminary work, and to Prof. Jin‐Quan Yu for insightful discussions. Financial support for this work was provided by Bristol‐Myers Squibb, the NIH (Grant CA134785 and a postdoctoral fellowship to M.R.L. GM082092‐02), and the Canadian Institutes of Health Research (postdoctoral fellowship to C.A.L.). ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200902761