90926-82-2Relevant academic research and scientific papers
Total synthesis and biological evaluation of an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid
Huang, Jinhua,Foyle, Dylan,Lin, Xiaorong,Yang, Jiong
, p. 9166 - 9173 (2013/10/08)
A convergent route has been developed to synthesize an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid and analogues. A Li/naphthalene- mediated reductive alkylation was employed for coupling β-cyclocitral and the corresponding benzyl chloride, while a BBr3-mediated one-pot bis-demethylation and intramolecular Friedel-Crafts alkylation was used to assemble the tricyclic molecular skeleton. The structure-activity relationship of the diterpenoid was assessed on the basis of antiproliferation assays of the natural product and analogues against strains of pathogenic yeasts and filamentous fungi.
Electrochemical generation and reaction of o-quinodimethanes from {[[2-(2,2-dibutyl-2-stannahexyl)phenyl]-methyl]thio} benzenes
Jinno, Madoka,Kitano, Yoshikazu,Tada, Masahiro,Chiba, Kazuhiro
, p. 435 - 437 (2008/02/12)
(equation presented) The anodic oxidation of {[[2-(2,2-dibutyl-2-stannahexyl)phenyl]methyl]thio}benzenes gave o-quinodimethanes which were trapped in situ by dienophiles to give the corresponding cycloadducts in excellent yields. The electron transfer and succeeding 1,4-elimination reaction was efficiently completed in a solution of lithium perchlorate/nitromethane in the presence of acetic acid. The reaction progress was quantitatively controlled by the passage of charge. By using this new method, an aryltetralin lignan skeleton was also synthesized.
