Oxidative C–C bond formation in heterocyclic chemistry

Abstract

There are remarkable advantages to be gained in terms of efficiency (lack of protecting groups, halogens, disposable functional groups), practicality (extremely concise sequences), stereocontrol (complete diastereoselectivity often observed), and conservation of oxidation state (oxidation state increases linearly in a synthesis by using innate functionality) when oxidative C-C bond formation is employed strategically. This account briefly highlights some of our work in this interesting area over the past two years, including total syntheses of the hapalindoles, fischerindoles, ketorolac, avrainvillamide, and stephacidins.