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.
Synthesis of Octahydroquinolizinones Aza-Analogues of Terpenoid Skeletons / A. Brandi; F. M. Cordero; C. Vurchio; M. Lucentini; S. Cicchi. - In: HETEROCYCLES. - ISSN 0385-5414. - STAMPA. - 84:(2012), pp. 1251-1258. [10.3987/COM-11-S(P)21]
Synthesis of Octahydroquinolizinones Aza-Analogues of Terpenoid Skeletons
BRANDI, ALBERTO;CORDERO, FRANCA MARIA;VURCHIO, CAROLINA;CICCHI, STEFANO
2012
Abstract
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.File | Dimensione | Formato | |
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