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

Yusuke OkanishiTohru IshikawaTakuya JinnouchiSatoshi HayashiToshikatsu TakanamiHiroshi AoyamaTakehiko Yoshimitsu
Published in: The Journal of organic chemistry (2023)
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.
Keyphrases
  • visible light
  • quantum dots
  • room temperature
  • diabetic rats
  • molecularly imprinted
  • oxidative stress
  • carbon dioxide
  • solid phase extraction