title: Application of a Palladium-Catalyzed C-H Functionalization/Indolization Method to Syntheses of cis-Trikentrin A and Herbindole B.
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.
authors: Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
authors: Raul A
authors: RA
authors: Leal
authors: Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
authors: Caroline
authors: C
authors: Bischof
authors: Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
authors: Youjin V
authors: YV
authors: Lee
authors: Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
authors: Shota
authors: S
authors: Sawano
authors: Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
authors: Christopher C
authors: CC
authors: McAtee
authors: Department of Bioengineering, University of California, Berkeley, Berkeley, CA, 94720, USA.
authors: Luke N
authors: LN
authors: Latimer
authors: Department of Bioengineering, University of California, Berkeley, Berkeley, CA, 94720, USA.
authors: Zachary N
authors: ZN
authors: Russ
authors: Department of Bioengineering, University of California, Berkeley, Berkeley, CA, 94720, USA. jdueber@berkeley.edu.
authors: John E
authors: JE
authors: Dueber
authors: Department of Chemistry, The Scripps Research Institute, La Jolla, CA, 92037, USA. yu200@scripps.edu.
authors: Jin-Quan
authors: JQ
authors: Yu
authors: Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA. rsarpong@berkeley.edu.
authors: Richmond
authors: 0000-0002-0028-6323
authors: R
authors: Sarpong
keywords: C−H activation; desymmetrization; indole alkaloids; indolization; natural products