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Synthesis 1986; 1986(10): 845-847
DOI: 10.1055/s-1986-31800
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A New Synthesis of 2,2-Disubstituted Cyclopentane-1,3-diones from Succinic Anhydride

I. D. Doyle* , R. A. Massy-Westropp, R. F. O. Warren
  • *Department of Organic Chemistry, University of Adelaide, Adelaide, 5001, Australia
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Publication Date:
20 August 2002 (online)

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Reaction of succinic anhydride (1) with (1-ethoxycarbonylethylidene) triphenylphosphorane (2) gives ethyl 2-(5-oxotetrahydrofur-2-ylidene) propanoate 3. Compound 3 is cleaved with sodium ethoxide to the ß-ketodiester anion, which is treated with alkylhalide to yield the 2,2-disubstituted ß-keto diester 4. Dieckmann cyclization of 4, followed by hydrolysis and decarboxylation, gives rise to 2,2-disubstituted cyclopentane-1,3-diones 5.

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