Total Synthesis of (−)-atrop-Abyssomicin C

Authors

  • Dr. Filip Bihelovic,

    Corresponding author
    1. Faculty of Chemistry, University of Belgrade, Studentski trg 16, POB 51, 11158 Belgrade 118 (Serbia)
    • Faculty of Chemistry, University of Belgrade, Studentski trg 16, POB 51, 11158 Belgrade 118 (Serbia)
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  • Prof. Dr. Radomir N. Saicic

    Corresponding author
    1. Faculty of Chemistry, University of Belgrade, Studentski trg 16, POB 51, 11158 Belgrade 118 (Serbia)
    • Faculty of Chemistry, University of Belgrade, Studentski trg 16, POB 51, 11158 Belgrade 118 (Serbia)
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  • Support from the Ministry of science and technological development is acknowledged (Project No. 172027). We are grateful to Prof. Vladimir Divjakovic (University of Novi Sad) for performing X-ray structural analysis, and to Prof. Milan Stojanovic (Columbia University) for helpful discussions.

Abstract

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Rolling in the deep: An enantioselective synthesis of a marine antibiotic (−)-atrop-abyssomicin C (see scheme) is described. The key steps of the synthetic sequence are the application of dual catalysis in the formation of the cyclohexane core, the gold-catalyzed formation of a tricyclic spirotetronate unit, and a highly efficient eleven-membered ring closure by a Nozaki–Hiyama–Kishi reaction.

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