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

Scheepers, Brent A; Klein, Rosalyn; Davies-Coleman, Michael T

Title: Synthesis of triprenylated toluquinone and toluhydroquinone metabolites from a marine-derived Penicillium fungus
Creator: Scheepers, Brent A
Creator: Klein, Rosalyn
Creator: Davies-Coleman, Michael T
Date Issued: 2006
Date: 2006
Type: Article
Identifier: vital:6592
Identifier: http://hdl.handle.net/10962/d1004341
Description: 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]
Format: 10 pages
Format: pdf
Language: English
Relation: 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. Available: http://dx.doi.org/10.1016/j.tetlet.2006.09.117

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Davies-Coleman, Michael Trevor (Prof)

Klein, Rosalyn (Assoc Prof)

RU Department of Chemistry

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