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Report | Regular issue | Vol 24, No. 6, 1986, pp.1589-1593
Published online, 1st January, 1970
DOI: 10.3987/R-1986-06-1589
Synthesis and Conformational Analysis of 9,10,11,12,12a,13-Hexahydro-7H-naphtho[1,2-b]quinolizidine

María Fernández, Gregorio G. Trigo, and Mónica M. Söllhuber*

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain

Abstract

The synthesis of 9,10,11,12,12a,13 -hexahydro-7H-naphtho[1,2-b]quinolizine, which has structural similarity to antitumor alkaloid cryptopleurine (1), has been accomplished by a sequence involving as a key step the Friedel-Crafts acylation of 1-(2-naphthylmethyl)pipecolinic acid (9). Ir,1H, and 13C nmr data indicate a trans-fused quinolizidine conformer for naphtho[1,2-b]quinolizidine (14).