Beilstein J. Org. Chem.2005,1, No. 11, doi:10.1186/1860-5397-1-11
/1860-5397-1-11 Abstract The synthesis of γ-functionalizedcyclopentenones 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 functionalizedcyclopentenones 4.
Keywords: Nef reaction; conjugated addition; nitroalkanes; 1,4-diketones; functionalizedcyclopentenones; 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-functionalizedcyclopentenones 4 via a
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Graphical Abstract
Scheme 1:
Synthesis of nitroalkanes derivatives 2 and their corresponding 1,4-diketones 3.