Abstract

11
D. A. Griffin, F. J. Leeper and J. Staunton
"Biomimetic Syntheses of Polyketide Aromatics from Pyrylium Salts"
J. Chem. Soc., Perkin Trans. 1,1984, 1035-1042. Full Text

Following attack by nucleophiles, various methoxypyrylium compounds derived from 2H-pyran-2-ones and 4H-pyran-4-ones react either to produce a linear b-polycarbonyl derivative in which one or more carbonyl groups is derivatised in the form of an enol ether or to form a methylene-2H-pyran. The linear polycarbonyl derivatives can undergo biomimetic cyclisation to generate polyketide aromatic systems; syntheses of the following benzene derivatives are described: ethyl 2,4-dimethoxy-6-methylbenzoate (29), 2,4-dimethoxy-6-methylbiphenyl (31), and 6-(2,4-dimethoxy-6-methylphenyl)-4-methoxy-2H-pyran-2-one (34).

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