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Short Paper | Special issue | Vol 84, No. 2, 2012, pp.1251-1258
Published online, 16th June, 2011
DOI: 10.3987/COM-11-S(P)21
Synthesis of Octahydroquinolizinones Aza-Analogues of Terpenoid Skeletons

Alberto Brandi,* Franca M. Cordero, Carolina Vurchio, Massimo Lucentini, and Stefano Cicchi

*Department of Chemistry "Ugo Schiff", University of Florence, Via della Lastruccia 13, 50019 Sesto Fiorentino (FI), Italy


Two new ketones, 6,6,9a-trimethyl-octahydro-quinolizin-2-one and 4,4,9a-trimethyl-octahydro-quinolizin-2-one, were synthesized by regioselective 1,3-dipolar cycloaddition of tetrahydropyridine nitrones with methylenecyclopropanes followed by thermal rearrangement. The new ketones feature a structural analogy with the 5,5,8a-trimethyl-octahydro-2-naphthalene skeleton typical of terpenoid structures.