Application of a Palladium‐Catalyzed C−H Functionalization/Indolization Method to Syntheses of <i>cis</i>‐Trikentrin A and Herbindole B

Abstract

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(sp 3 )−H amination/indole formation. Studies toward a selective desymmetrization of the meso ‐hydroquinone are also reported.