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

Yusuke Okanishi, Tohru Ishikawa, Takuya Jinnouchi, Satoshi Hayashi, Toshikatsu Takanami, Hiroshi Aoyama, Takehiko Yoshimitsu

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)1085-1092
Number of pages8
JournalJournal of Organic Chemistry
Volume88
Issue number2
DOIs
Publication statusPublished - Jan 20 2023

ASJC Scopus subject areas

  • Organic Chemistry

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