Total Synthesis of (+)-Yatakemycin

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  • Kentaro Okano
    Graduate School of Pharmaceutical Sciences, University of Tokyo, PRESTO, Japan Science and Technology Agency, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
  • Hidetoshi Tokuyama
    Graduate School of Pharmaceutical Sciences, University of Tokyo, PRESTO, Japan Science and Technology Agency, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
  • Tohru Fukuyama
    Graduate School of Pharmaceutical Sciences, University of Tokyo, PRESTO, Japan Science and Technology Agency, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

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<jats:title>Abstract</jats:title><jats:p>A convergent total synthesis of (+)‐yatakemycin was accomplished by a 20‐step sequence in 13 % overall yield. The regioselective ring opening of (<jats:italic>S</jats:italic>)‐epichlorohydrin with a 2,6‐dibromophenyllithium derivative enabled us to introduce a chiral carbon center, which was required for the stereoselective construction of the cyclopropane ring. The five aryl–nitrogen bonds in (+)‐yatakemycin were constructed by a mild copper‐mediated aryl amination that utilized the combination of CuI with CsOAc. The efficient and chemoselective debenzylation of aryl benzyl ether with BCl<jats:sub>3</jats:sub> in the presence of pentamethylbenzene was developed. With these new methodologies, the subgram‐scale synthesis of (+)‐yatakemycin was achieved.</jats:p>

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