ol7b02005_si_001.pdf (5.27 MB)
Cascade Radical Cyclization of N‑Propargylindoles: Substituents Dictate Stereoselective Formation of N‑Fused Indolines versus Indoles
journal contribution
posted on 2017-09-13, 17:44 authored by Santosh J. Gharpure, Yogesh G. ShelkeAn 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.