Tetrahedron

Cyclopentenones from 1, 2-disiloxycyclobutene via silylated 1-vinylcylopropanols. Application to the synthesis of dihydrojasmone and cis-jasmone

J Salaün, Y Almirantis

Index: Salauen, J.; Almirantis, Y. Tetrahedron, 1983 , vol. 39, # 14 p. 2421 - 2428

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Citation Number: 25

Abstract

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.