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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
Author(s) -
Moustafa Gamal A. I.,
Suizu Hiroshi,
Aoyama Hiroshi,
Arai Masayoshi,
Akai Shuji,
Yoshimitsu Takehiko
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201400110
Subject(s) - aromatization , chemistry , cytotoxicity , stereochemistry , enantiomer , halogenation , combinatorial chemistry , organic chemistry , in vitro , catalysis , biochemistry
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.