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

Org Lett

The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Published: April 2022

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.

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http://dx.doi.org/10.1021/acs.orglett.2c00948DOI Listing

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