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. Issue 6 (2nd April 2014)

• Record Type: Journal Article
• Authors: Moustafa, Gamal A. I.; Suizu, Hiroshi; Aoyama, Hiroshi; Arai, Masayoshi; Akai, Shuji; Yoshimitsu, Takehiko
• Is Part Of: Chemistry, an Asian journal. Volume 9:Issue 6(2014:Jun.)
• Page Start: 1506
• Page End: 1510
• Publication Date: 2014-04-02
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201400110
• Languages: English
• ISSNs: 1861-4728

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A facile enantiospecific approach to (+)‐ligudentatol (<bold>1</bold>) and (−)‐ligudentatol (<italic>ent</italic>‐<bold>1</bold>) 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.</p> </abstract>