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Issue 0, 1984
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Dioxolanones as synthetic intermediates. Part 2. Synthesis of tetronic acids and pulvinones

Abstract

The utility of 1,3-dioxolan-4-ones as intermediates in the synthesis of tetronic acids is examined. The reaction of dioxolanone (1) with lithium enolates of 2-substituted methyl or t-butyl acetates at –78 °C in tetrahydrofuran afforded a general synthesis of 2-substituted tetronic acids (3)–(8). Treatment of (1) with the anions of 2-substituted acetonitriles led to formation of the corresponding 3-substituted-2-aminofuran-4(5H)-ones (13) and (14).

A route to unsymmetrically substituted pulvinones by reaction of 5-arylidene-2,2-pentamethylene-1,3-dioxolan-4-ones [5′-arylidenecyclohexanespiro-2′(1′,3′-dioxolan)-4′-ones] with appropriately substituted phenylacetic ester anions has been devised. Thus, the preparation of the naturally occurring pigment 3′,4′,4-trihydroxypulvinone (18) was achieved via an intermediate in which the phenolic groups were protected as benzyl ethers. The dioxolanone (26) has been used in the preparation of 2-acyl-4-benzylidenetetronic acids.

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Article type: Paper
DOI: 10.1039/P19840001539
Citation: J. Chem. Soc., Perkin Trans. 1, 1984, 1539-1545
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    Dioxolanones as synthetic intermediates. Part 2. Synthesis of tetronic acids and pulvinones

    R. Ramage, G. J. Griffiths, F. E. Shutt and J. N. A. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1984, 1539
    DOI: 10.1039/P19840001539

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