CYCLOPENTENONES FROM 1,2-DISILOXYCYCLOBUTENE VIA SILYLATED 1-VINYLCYCLOPROPANOLS. APPLICATION TO THE SYNTHESIS OF DIHYDROJASMONE AND CIS-JASMONE
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.
Salauen, J.,Almirantis, Y.
p. 2421 - 2428
(2007/10/02)
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