Shortcut Approach to Cyclopenta[b]indoles by [3+2] Cyclodimerization of Indole-Derived Cyclopropanes

Abstract

A new straightforward approach to 3-indolyl-derived cyclopenta[b]indoles by a Lewis acid triggered [3+2] cyclodimerization of 2-(3-indolyl)cyclopropane-1,1-dicarboxylic acid diesters was developed. This reaction exhibits exceptional chemo-, regio-, and diastereoselectivities, leading to the formation of an individual diastereomer with a relative configuration that corresponds to that of naturally occurring indole terpenoids.

Key words

annulations - dimerizations - fused-ring systems - indoles - regioselectivity - stereoselectivity

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