4.7 Article

Copper-Catalyzed Cyclization/Dimerization of Tryptamines with O2/Air as the Sole Oxidant: Direct Access to Complex Bispyrrolidino[2,3-b]indoline

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 23, Pages 17164-17172

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02277

Keywords

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Funding

  1. NSFC [22061010]
  2. Guizhou Province Science and Technology Foundation, china [QKHJC[2019]1214]
  3. CAS Light of West China Program
  4. Guizhou Provincial Thousands of Innovative and Entrepreneurial Talents program [GZQ202006080]

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The novel indoline scaffold was synthesized using transition metal catalysis and environmentally friendly oxidant O-2/air. Different from traditional methods, a copper-catalyzed oxidative reaction was developed and demonstrated for the synthesis of various natural products.
The first transition metal catalytic one-step synthesis of the 3a, 3a'-bispyrrolidino [2,3-b] indoline scaffold via tandem cyclization/dimerization of tryptamines has been realized with the environmentally friendly O-2/air as the sole oxidant. Different from the traditional direct oxidation of indole N-H group by excess amount of metal salts, a copper-catalyzed oxidative cyclization reaction is developed for the formation of the radical pyrrolidinoindoline intermediate in the current strategy. The robustness and practicality of this methodology is demonstrated by the step-economic, divergent total synthesis of natural products (+/-)-folicanthine and meso-folicanthine.

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