4.8 Article

Total Synthesis of Hapalindole-Type Natural Products

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 50, Pages 13840-13844

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406626

Keywords

hapalindole; indole terpenoids; Prins cyclization

Funding

  1. Ministry of Science Technology [2013CB836900]
  2. National Natural Science Foundation of China [21290180, 21172235, 21222202]
  3. Pujiang Program [12J1410800]
  4. China Postdoctoral Science Foundation [2014M551480]

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A unified and bioinspired oxidative cyclization strategy was used in the first total syntheses of naturally occurring 12-epi-hapalindoleQ isonitrile, hapalonamideH, deschloro 12-epi-fischerindoleI nitrile, and deschloro 12-epi-fischerindoleW nitrile, as well as the structural revision of the latter. HapalindolesH and Q were also synthesized.

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