Identification of a Novel Michael Acceptor Group for the Reversible Addition of Oxygen- and Sulfur-Based Nucleophiles. Synthesis and Reactivity of the 3-Alkylidene-3<i>H</i>-indole 1-Oxide Function of Avrainvillamide

Abstract

The 3-alkylidene-3H-indole 1-oxide functional group found in the naturally occurring alkaloid avrainvillamide has been synthesized by a cross coupling−reductive condensation sequence and found to undergo reversible addition of oxygen- and sulfur-based nucleophiles