A convenient synthesis of γ-functionalized cyclopentenones

• Nour Lahmar,
• Taïcir Ben Ayed,
• Moncef Bellassoued and
• Hassen Amri

Beilstein J. Org. Chem. 2005, 1, No. 11, doi:10.1186/1860-5397-1-11

• /1860-5397-1-11 Abstract The synthesis of γ-functionalized cyclopentenones was carried out in a few steps, starting firstly with the preparation of nitroketonic intermediates 2, which were readily transformed into 1,4-diketones using the Nef conversion. The intramolecular cyclization of the γ-diketones

• 3 in a basic medium, led to the functionalized cyclopentenones 4. Keywords: Nef reaction; conjugated addition; nitroalkanes; 1,4-diketones; functionalized cyclopentenones; Introduction The cyclopentenones are considered as an important class of compounds because they are present in a large variety

• of natural products and in many important biologically active compounds [1][2][3][4][5][6] such as prostanoids, jasmonoids, rethrolones, methylenomycins and allylrethrones. In this paper, we wish to describe a new synthetic procedure for the preparation of γ-functionalized cyclopentenones 4 via a