Radical-Based Route to Functionalized Tetralin: Formal Total Synthesis of (±)-Hamigeran B

J Org Chem. 2023 Jan 20;88(2):1085-1092. doi: 10.1021/acs.joc.2c02552. Epub 2023 Jan 10.

Abstract

A formal synthetic route to hamigeran B, an antiviral marine natural product with a unique tricyclic molecular architecture, has been developed. The key chemical transformations in the present route include a novel zinc(II)porphyrin-catalyzed photoredox radical cascade cyclization to access a functionalized tetralin, a catalyst-free benzylic radical bromination with NBS by visible-light irradiation, and a samarium(II)-induced cyclization of brominated tetralone possibly via an orthoquinodimethane-like intermediate.