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Convergent Synthesis of (−)-Quinocarcin Based on the Combination of Sonogashira Coupling and Gold(I)-Catalyzed 6-endo-dig Hydroamination

Authors

  • Hiroaki Chiba,

    1. Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501 (Japan), Fax: (+81) 75-753-4570
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  • Yuki Sakai,

    1. Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501 (Japan), Fax: (+81) 75-753-4570
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  • Ayako Ohara,

    1. Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501 (Japan), Fax: (+81) 75-753-4570
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  • Dr. Shinya Oishi,

    1. Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501 (Japan), Fax: (+81) 75-753-4570
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  • Prof. Dr. Nobutaka Fujii,

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501 (Japan), Fax: (+81) 75-753-4570
    • Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501 (Japan), Fax: (+81) 75-753-4570
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  • Prof. Dr. Hiroaki Ohno

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501 (Japan), Fax: (+81) 75-753-4570
    • Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501 (Japan), Fax: (+81) 75-753-4570
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Abstract

The total synthesis of the pentacyclic tetrahydroisoquinoline alkaloid quinocarcin, which possesses intriguing structural and biological features, has been achieved through a gold(I)-catalyzed regioselective hydroamination reaction. It is noteworthy that the regioselectivity of the intramolecular hydroamination of an unsymmetrical alkyne could be completely switched through substrate control. Other key features of this synthesis include the highly stereoselective synthesis of 2,5-cis-pyrrolidine through the intramolecular amination of the bromoallene and the Lewis acid mediated ring opening of dihydrobenzofuran.

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