Total Synthesis of Actinophyllic Acid

Yu Yoshii, Hidetoshi Tokuyama, David Y.K. Chen

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Herein we report a total synthesis of the indolohydroazocine natural product actinophyllic acid. The target molecule was retrosynthetically deconvoluted to render a greatly simplified and symmetrical [4.4.1] bicyclic trienone, the desymmetrization of which was carefully examined under a variety of conditions, including oxidative, reductive, and transition-metal-catalyzed transformations. Ultimately, the successful synthetic strategy featured chemoselective catalytic dihydroxylation, desymmetrizing nitrile oxide dipolar cycloaddition, and palladium-catalyzed aminoarylation to sequentially modify the three olefins within the trienone, followed by a late-stage reductive cascade indolization and alkylation to complete the target molecule.

Original languageEnglish
Pages (from-to)12277-12281
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number40
DOIs
Publication statusPublished - 2017 Sep 25

Keywords

  • alkaloids
  • cycloaddition
  • desymmetrization
  • natural products
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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