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Paper | Regular issue | Vol 29, No. 3, 1989, pp.477-484
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4787
■ Synthesis of (±)-(2R*,11bS*)-3’-Aryl-9,10-dimethoxy-1,3,4,5,7,11b-hexahydrospiro[benzo[a]quinolizin-2,5’-oxazolidine]-2’,4’-diones

J. Carlos Menéndez, Carmen Avendaño, 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 (±)-(2R*,11bS*)-3’-aryl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydrospiro[benzo[α] quinolizin-2,5’-oxazolidine]-2’,4’-diones (1) was achieved by two alternative routes involving the treatment of cyanohydrin 3 with aryl isocyanates via 4-imino derivatives 5 and 6 or the cyclization of the hydroxy ester 9 with aryl isocyanates. Compounds 1 present a trans Conformation in the quinolizidine system and exist in a (2R*,11bS*) configuration.