5 years ago

Total Synthesis of Actinophyllic Acid

Total Synthesis of Actinophyllic Acid
David Y.-K. Chen, Yu Yoshii, Hidetoshi Tokuyama
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. Find a mirror to break: The indolohydroazocine natural product actinophyllic acid was synthesized by an expedient route based on the desymmetrization of a trienone precursor. The developed synthesis features chemoselective catalytic dihydroxylation of the trienone, desymmetrizing dipolar cycloaddition with a nitrile oxide, and palladium-catalyzed aminoarylation as key steps.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201706312

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