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Synlett 2000; 2000(6): 0883-0886
DOI: 10.1055/s-2000-6724
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An Efficient Total Synthesis of (-)-Vindoline

Satoshi Kobayashi* , Toshihiro Ueda, Tohru Fukuyama
  • *Graduate School of Pharmaceutical Sciences, University of Tokyo, CREST, The Japan Science and Technology Corporation (JST), 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan; Fax +81-3-5802-8694; E-mail: fukuyama@mol.f.u-tokyo.ac.jp
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Publication Date:
31 December 2000 (online)

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A highly efficient total synthesis of the title compound is described. Our synthesis features a highly efficient preparation of the key intermediate 11 using our novel indole synthesis methodology. A novel amine protecting protocol by means of 2,4-dinitrobenzenesulfonamides has been developed to ensure the formation of the elusive secodine-type intermediate 15 under very mild conditions.

vindoline - tin-mediated indole synthesis - total synthesis - 2,4-dinitrobenzenesulfonamide - 11-hydroxytabersonine