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Application of a Palladium‐Catalyzed C−H Functionalization/Indolization Method to Syntheses of cis‐Trikentrin A and Herbindole B |
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| Authors: | Raul A. Leal Caroline Bischof Youjin V. Lee Shota Sawano Christopher C. McAtee Luke N. Latimer Zachary N. Russ Prof. John E. Dueber Prof. Jin‐Quan Yu Prof. Richmond Sarpong |
| Affiliation: | 1. Department of Chemistry, University of California, Berkeley, Berkeley, CA, USA;2. Department of Bioengineering, University of California, Berkeley, Berkeley, CA, USA;3. Department of Chemistry, The Scripps Research Institute, La Jolla, CA, USA |
| 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. |
| Keywords: | C− H activation desymmetrization indole alkaloids indolization natural products |