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Overturning Indolyne Regioselectivities and Synthesis of Indolactam V

Overturning Indolyne Regioselectivities and Synthesis of Indolactam V

Sarah M Bronner, Adam E Goetz, Neil K Garg

J Am Chem Soc. 2011 Mar 23;133(11):3832-5.

PMID: 21351773

Abstract:

We report the design and synthesis of an indolyne that displays a reversal in regioselectivity, in both nucleophilic addition and cycloaddition reactions, compared to typical 4,5-indolynes. Our approach utilizes simple computations to predict regioselectivity in reactions of unsymmetrical arynes. With this methodology, novel benzenoid-substituted indoles can be accessed with significant regiocontrol. Furthermore, the technology provides an unconventional tactic for the synthesis of C4-substituted indole alkaloids, as demonstrated by a synthesis of indolactam V.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP90365574	(−)-Indolactam V		90365-57-4	Price

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