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Cascade Radical Cyclization of N-Propargylindoles: Substituents Dictate Stereoselective Formation of N-Fused Indolines versus Indoles

Author:
Gharpure, Santosh J., Shelke, Yogesh G.
Source:
Organic letters 2017 v.19 no.19 pp. 5022-5025
ISSN:
1523-7052
Subject:
carbon, chemical structure, cyclization reactions, indoles, nitrogen, stereoselectivity, sulfides
Abstract:
An efficient protocol for the synthesis of pyrrolo[1,2-a]indole derivatives having sulfide functionality using cascade radical cyclization on propargylindole is described. The nature of the substituents at the propargylic carbon bearing nitrogen of the indole has a profound effect on the rate, yield, and nature of the product obtained by the cascade radical cyclization. An expeditious one-pot route for cascade radical cyclization–desulfurization is also presented. Products obtained were elaborated to the core of the putative structure of the yuremamine and indoline derivative with five contiguous stereocenters.
Agid:
5826917