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.

Iron porphyrin-catalysed C(sp3)–H amination with alkyl azides for the synthesis of complex nitrogen-containing compounds

“…Some of these alkaloids exhibit potent anticancer activity, 51 and their intriguing structures have been attracting the attention of organic chemists. [52][53][54] As shown in Scheme 3, azide 6 underwent intramolecular unactivated C(sp 3 )-H amination to afford 7 in 95% yield, from which (±)-mesembrane could be obtained according to the reported procedure. 55…”