Synthesis of triprenylated toluquinone and toluhydroquinone metabolites from a marine-derived Penicillium fungus

Scheepers, B.A. and Klein, R. and Davies-Coleman, M.T. (2006) Synthesis of triprenylated toluquinone and toluhydroquinone metabolites from a marine-derived Penicillium fungus. Tetrahedron Letters, 47 (47). pp. 8243-8246. ISSN 0040-4039

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Official URL: http://dx.doi.org/10.1016/j.tetlet.2006.09.117

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. Graphical abstract: Marine fungal metabolites 1 and 2 were synthesized from 2-methyl-1,4-benzoquinone in four and five steps, respectively. [For graphic image see full-text version]

Item Type:Article
Uncontrolled Keywords:Penicillium; Marine fungus; Triprenyl; Toluhydroquinone; Toluquinone
Subjects:Y Unknown > Subjects to be assigned
Divisions:Faculty > Faculty of Science > Chemistry
ID Code:421
Deposited By:INVALID USER
Deposited On:23 Oct 2006
Last Modified:06 Jan 2012 16:18
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