4.8 Article

Collective Synthesis of Cladiellins Based on the Gold-Catalyzed Cascade Reaction of 1,7-Diynes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 7, Pages 1837-1840

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201309449

Keywords

cascade reaction; cyclization; gold; natural products; total synthesis

Funding

  1. National Basic Research Program of China (973 Program) [2009CB940904]
  2. National 863 Program [2013AA092903]

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The cladiellin family of natural products, which includes molecules with various biological activities, continues to invite new synthetic studies. A gold-catalyzed tandem reaction of 1,7-diynes to construct the 6-5-bicyclic ring systems that are present in a number of natural products was developed. This reaction was applied as the key step to realize the formal and total syntheses of nine members of the cladiellin family in an enantio- and diastereoselective manner. This modular and efficient approach could also be used for the construction of other cladiellins, as well as their analogues, for follow-up studies.

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