Oxocyclopentenol Syntheses

Article abstract of DOI:10.1021/jo00224a003

Metal-assisted decomposition of α-diazo carbonyl compounds in 1,2-dialkoxy-1-alkenes are shown to yield β,β'-dialkoxycyclopropyl carbonyl systems, whose acid hydrolysis produces α-alkoxy-γ-dicarbonyl substances.Intramolecular condensations of the latter lead to oxocyclopentenols.Application of this reaction scheme to the syntheses of a prostaglandin intermediate and of tetrahydropyrethrolone is described.