Application of a Palladium‐Catalyzed C−H Functionalization/Indolization Method to Syntheses of cis‐Trikentrin A and Herbindole B. (29th August 2016)

• Record Type: Journal Article
• 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
• Is Part Of: Angewandte Chemie. Volume 128:Number 39(2016)
• Page Start: 12003
• Page End: 12007
• Publication Date: 2016-08-29
• Subjects: C-H-Aktivierung -- Desymmetrisierungen -- Indol-Alkaloide -- Indolisierung -- Naturstoffe; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201605475
• Languages: English
• ISSNs: 0044-8249

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.