Abstract
2,2-Disubstituted indoxyls are commonly found within natural products and bioactive
molecules. Among the numerous methods to access such motifs, the dearomative transformation
of indoles represents an attractive approach. Despite much development, a potential
gap exists in the oxidative union of readily accessible 2-substituted indoles with
nucleophilic partners, where a general transformation accommodating 2-alkyl substitution
and a broad range of nucleophiles is lacking. Herein, we describe the development
of a user-friendly solution to this challenge and highlight its utility in the synthesis
of complex alkaloids.
1 Introduction
2 Synthesis of 2,2-Disubstituted Indoxyls via Dearomatization of Indoles: Background
3 Oxidative Dearomatization of 2-Alkylindoles to 2,2-Disubstituted Indoxyls: Development
4 Selected Scope and Preliminary Investigations toward an Asymmetric Coupling
5 Application to the Total Synthesis of Complex Alkaloids
6 Conclusions
Key words
indoxyl - alkaloids - synthetic methods - total synthesis - dearomatization
