Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 11, Pages 3832-3835Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja200437g
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Funding
- NIH-NIGMS [R01 GM090007]
- Boehringer Ingelheim
- DuPont
- Eli Lilly
- Foote Fellowship
- University of California, Los Angeles
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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.
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