4.7 Article

Azaanthraquinone Assembly from N-Propargylamino Quinone via a Au(I)-Catalyzed 6-endo-dig Cycloisomerization

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 12, Pages 4323-4325

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo1006637

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Funding

  1. National Science Foundation of China [20802034]
  2. Natural Science Foundation of Jiangsu Province [BK 2009229]
  3. 973 Program [200703936404]

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A methodology to assemble the azaanthraquinone skeleton from N-propargylamino quinone by a Au(I)-catalyzed 6-endo-dig cycloisomerization was developed. The catalytic process was applied to the synthesis of alkaloid cleistopholine and its analogues. A mechanism involving benign nucleophilicity of the aminoquinone was proposed.

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