Synthesis of new cyclopentenones from phenacylfurans
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Substituted cyclopentenones are known as precursors of modified prostaglandins [1,2] and compounds displaying various kinds of biological activity . Despite the many methods for the preparation of cyclopente-nones, there have been only a few methods described for the synthesis of such systems containing an acyl group [4, 5, 6]. 1,4-Dicarbonyl compounds (in one-step procedures) or furan derivatives (in two-step procedures) have often been used as starting compounds . There have been only very few examples of the preparation of cyclopentenones from furans in one step [6,8,9]. We propose the use of phenacylfurans 1 recently obtained in our laboratory  for this purpose.
Indeed, we have found that the treatment of phenacylfurans 1a,b with a mixture of acetic and hydrochlo-ric acids leads to cyclopentenones 2 and 3. The reaction proceeds at room temperature in good yield. 1H NMR spectra of the crude product mixtures indicated the formation of isomeric cyclopentenones 2 and 3in...
Keywordsphenacylfurans furans cyclopentenones recyclization
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