Enantiospecific synthesis and cytotoxicity evaluation of ligudentatol: A programmed aromatization approach to the 2,3,4-trisubstituted phenolic motif via visible-light-mediated group transfer radical cyclization

Gamal A.I. Moustafa, Hiroshi Suizu, Hiroshi Aoyama, Masayoshi Arai, Shuji Akai, Takehiko Yoshimitsu

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A facile enantiospecific approach to (+)-ligudentatol (1) and (-)-ligudentatol (ent-1) is reported. The approach features the construction of a trisubstituted phenolic motif fused to a chiral aliphatic ring by a sequence of visible-light-mediated radical seleno transfer cyclization, bromination, concomitant selenoxide elimination-dehydrobromination, and demethoxycarbonylation, namely, a programmed aromatization. Biological evaluation of the enantiomers of ligudentatol obtained by the present route revealed for the first time their cytotoxicity towards various cancer cell lines. Light gifts: A facile enantiospecific approach to (+)-ligudentatol (1) and (-)-ligudentatol (ent-1) is reported. The approach features the construction of a trisubstituted phenolic motif fused to a chiral aliphatic ring by a sequence of visible-light-mediated seleno transfer radical cyclization, bromination, concomitant selenoxide elimination-dehydrobromination, and demethoxycarbonylation, that is, a programmed aromatization.

Original languageEnglish
Pages (from-to)1506-1510
Number of pages5
JournalChemistry - An Asian Journal
Volume9
Issue number6
DOIs
Publication statusPublished - Jun 2014

Keywords

  • cytotoxicity
  • natural products
  • radical reactions
  • seleno transfer
  • total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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