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- Title
Application of a Palladium-Catalyzed C−H Functionalization/Indolization Method to Syntheses of cis-Trikentrin A and Herbindole B.
- Authors
Leal, Raul A.; Bischof, Caroline; Lee, Youjin V.; Sawano, Shota; McAtee, Christopher C.; Latimer, Luke N.; Russ, Zachary N.; Dueber, John E.; Yu, Jin ‐ Quan; Sarpong, Richmond
- Abstract
We describe herein formal syntheses of the indole alkaloids cis-trikentrin A and herbindole B from a common meso-hydroquinone intermediate prepared by a ruthenium-catalyzed [2+2+1+1] cycloaddition that has not been used previously in natural product synthesis. Key steps include a sterically demanding Buchwald-Hartwig amination as well as a unique C(sp3)−H amination/indole formation. Studies toward a selective desymmetrization of the meso-hydroquinone are also reported.
- Subjects
PALLADIUM catalysts; INDOLE alkaloids; HYDROQUINONE; RUTHENIUM catalysts; RING formation (Chemistry)
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 39, p12003
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201605475