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Total Synthesis of (−)-Conophylline and (−)-Conophyllidine

Authors

  • Dr. Yuki Han-ya,

    1. Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-4777
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  • Prof. Dr. Hidetoshi Tokuyama,

    1. Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-4777
    2. Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai 985-8578 (Japan)
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  • Prof. Dr. Tohru Fukuyama

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-4777
    • Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-4777
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  • This work was financially supported by KAKENHI and JSPS (predoctoral fellowship for Y. H.), and the “Funding Program for Next Generation World-Leading Researchers”, Cabinet Office, Government of Japan (for H.T.). We thank Prof. K. Umezawa for providing the natural sample of conophylline.

Abstract

original image

Double take: The total syntheses of the title compounds were accomplished in a highly convergent manner. The approach features the regio- and diastereoselective Polonovski–Potier-type reaction for the coupling of two aspidosperma skeletons and the formation of the dihydrofuran ring. Troc=2,2,2-trichloroethoxycarbonyl.

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