1621082-58-3Relevant academic research and scientific papers
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
Moustafa, Gamal A. I.,Suizu, Hiroshi,Aoyama, Hiroshi,Arai, Masayoshi,Akai, Shuji,Yoshimitsu, Takehiko
, p. 1506 - 1510 (2014/06/09)
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.
