Synthesis of triprenylated toluquinone and toluhydroquinone metabolites from a marine-derived Penicillium fungus |
| |
Authors: | Brent A Scheepers |
| |
Institution: | Department of Chemistry, Rhodes University, Grahamstown 6140, South Africa |
| |
Abstract: | Two triprenylated toluquinone and toluhydroquinone marine fungal metabolites, 5-methyl-2-(2′E,6′E)-3′,7′,11′-trimethyl-2′,6′,10′-dodecatrienyl]-2,5-cyclohexadiene-1,4-dione and 5-methyl-2-(2′E,6′E)-3,7,11-trimethyl-2′,6′,10′-dodecatrienyl]-1,4-benzenediol, were synthesized in four and five steps, respectively, from 2-methyl-1,4-benzoquinone. The synthesis extends the applicability of the oxidative ether cleavage of hydroquinone dimethyl ethers with argentic oxide under acidic conditions to include the oxidative demethylation of polyprenylated-1,4-dimethoxy-toluhydroquinones with a quantitative survival of the oxidation- and acid-sensitive polyprenyl side chain. |
| |
Keywords: | Penicillium Marine fungus Triprenyl Toluhydroquinone Toluquinone |
本文献已被 ScienceDirect 等数据库收录! |
|