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Overturning indolyne regioselectivities and synthesis of indolactam V.

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.

SUBMITTER: Bronner SM

PROVIDER: S-EPMC3060274 | biostudies-literature | 2011 Mar

REPOSITORIES: biostudies-literature

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Overturning indolyne regioselectivities and synthesis of indolactam V.

Bronner Sarah M SM Goetz Adam E AE Garg Neil K NK

Journal of the American Chemical Society 20110225 11

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-substitute ...[more]

PMID: 21351773

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