Wiley
Chemistry - An Asian Journal
,  volume 9 ,  issue 6 ,  pages 1506-1510

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

Publication type: Journal Article
Publication date: 2014-04-02
Wiley
scimago Q2
wos Q2
SJR: 0.751
CiteScore: 5.9
Impact factor: 3.3
ISSN: 18614728, 1861471X
General Chemistry
Organic Chemistry
Biochemistry
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.
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Moustafa G. A. I. et al. 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 // Chemistry - An Asian Journal. 2014. Vol. 9. No. 6. pp. 1506-1510.
GOST all authors (up to 50) Copy
Moustafa G. A. I., Suizu H., Aoyama H., Arai M., Akai S., Yoshimitsu T. 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 // Chemistry - An Asian Journal. 2014. Vol. 9. No. 6. pp. 1506-1510.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1002/asia.201400110
UR - https://doi.org/10.1002/asia.201400110
TI - 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
T2 - Chemistry - An Asian Journal
AU - Moustafa, Gamal A. I.
AU - Suizu, Hiroshi
AU - Aoyama, Hiroshi
AU - Arai, Masayoshi
AU - Akai, Shuji
AU - Yoshimitsu, Takehiko
PY - 2014
DA - 2014/04/02
PB - Wiley
SP - 1506-1510
IS - 6
VL - 9
PMID - 24700669
SN - 1861-4728
SN - 1861-471X
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2014_Moustafa,
author = {Gamal A. I. Moustafa and Hiroshi Suizu and Hiroshi Aoyama and Masayoshi Arai and Shuji Akai and Takehiko Yoshimitsu},
title = {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},
journal = {Chemistry - An Asian Journal},
year = {2014},
volume = {9},
publisher = {Wiley},
month = {apr},
url = {https://doi.org/10.1002/asia.201400110},
number = {6},
pages = {1506--1510},
doi = {10.1002/asia.201400110}
}
MLA
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MLA Copy
Moustafa, Gamal A. I., et al. “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.” Chemistry - An Asian Journal, vol. 9, no. 6, Apr. 2014, pp. 1506-1510. https://doi.org/10.1002/asia.201400110.