Synthesis of Noraugustamine and Development of an Oxidative Heck/Aza-Wacker Cascade Cyclization.

Abstract

Radical and transition metal-catalyzed cascade cyclization strategies were investigated with respect to the synthesis of the tetracyclic core of the augustamine-type Amaryllidaceae alkaloids. These studies resulted in the synthesis of noraugustamine and the development of an oxidative Heck/aza-Wacker cascade forming two rings, a C-N bond, and an all-carbon quaternary center in a single step.