Organocatalytic Site-Selective Acylation of 10-Deacetylbaccatin III

  • Yanagi Masanori
    Institute for Chemical Research, Kyoto University
  • Ninomiya Ryo
    Institute for Chemical Research, Kyoto University
  • Ueda Yoshihiro
    Institute for Chemical Research, Kyoto University
  • Furuta Takumi
    Institute for Chemical Research, Kyoto University
  • Yamada Takeshi
    Kitasato Institute for Life Sciences, Kitasato University Graduate School of Infection Control Sciences, Kitasato University
  • Sunazuka Toshiaki
    Kitasato Institute for Life Sciences, Kitasato University Graduate School of Infection Control Sciences, Kitasato University
  • Kawabata Takeo
    Institute for Chemical Research, Kyoto University

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Organocatalytic site-selective diversification of 10-deacetylbaccatin III, a key natural product for the semisynthesis of taxol, has been achieved. Various acyl groups were selectively introduced into the C(10)–OH of 10-deacetylbaccatin III. The C(10)–OH selective acylation was also applied to acylative site-selective dimerization of 10-deacetylbaccatin III to provide the structurally defined dimer.

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