CYCLOPENTENONES FROM 1,2-DISILOXYCYCLOBUTENE VIA SILYLATED 1-VINYLCYCLOPROPANOLS. APPLICATION TO THE SYNTHESIS OF DIHYDROJASMONE AND CIS-JASMONE

Article abstract of DOI:10.1016/S0040-4020(01)91969-6

An effective synthesis of 2,3-disubstituted 2-cyclopentenones involves C₄ - C₃ ring contraction of the readily available 1,2-disiloxycyclobutene followed by thermal C₃ - C₅ ring enlargement of trimethylsiloxyvinyl-cyclopropanes.To illustrate the convenience of this new approach the total syntheses of 2-methyl-3-p-tolyl-2-cyclopentenone, dihydrojasmone, and cis-jasmone are reported.