TY - JOUR
T1 - Enantiospecific synthesis and cytotoxicity evaluation of ligudentatol
T2 - A programmed aromatization approach to the 2,3,4-trisubstituted phenolic motif via visible-light-mediated group transfer radical cyclization
AU - Moustafa, Gamal A.I.
AU - Suizu, Hiroshi
AU - Aoyama, Hiroshi
AU - Arai, Masayoshi
AU - Akai, Shuji
AU - Yoshimitsu, Takehiko
PY - 2014/6
Y1 - 2014/6
N2 - 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.
AB - 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.
KW - cytotoxicity
KW - natural products
KW - radical reactions
KW - seleno transfer
KW - total synthesis
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U2 - 10.1002/asia.201400110
DO - 10.1002/asia.201400110
M3 - Article
C2 - 24700669
AN - SCOPUS:84901231651
SN - 1861-4728
VL - 9
SP - 1506
EP - 1510
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
IS - 6
ER -
