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Exploration of a KI-catalyzed oxidation system for direct construction of bispyrrolidino[2,3-b]indolines and the total synthesis of (+)-WIN 64821

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Abstract

A facile and environmentally benign KI(cat.)/NaBO3·4H2O oxidation system has been developed for the tandem oxidative aminocyclization/coupling of tryptamines, affording a series of 3a,3a′-bispyrrolidino[2,3-b]indolines with high efficiency (up to 94% yield). This reaction features an electrophilic “I+” mechanism, which is importantly quite different from and milder than the typical radical-involving process, and can be readily amplified for the total synthesis of (+)-WIN 64821.

Graphical abstract: Exploration of a KI-catalyzed oxidation system for direct construction of bispyrrolidino[2,3-b]indolines and the total synthesis of (+)-WIN 64821

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Publication details

The article was received on 06 Nov 2019, accepted on 25 Nov 2019 and first published on 26 Nov 2019


Article type: Communication
DOI: 10.1039/C9CC08646C
Chem. Commun., 2020, Advance Article

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    Exploration of a KI-catalyzed oxidation system for direct construction of bispyrrolidino[2,3-b]indolines and the total synthesis of (+)-WIN 64821

    S. Chen, J. Yang, K. Dai, F. Zhang, X. Zhang and Y. Tu, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC08646C

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