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Paper | Regular issue | Vol 32, No. 3, 1991, pp.469-476
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5601
Synthesis and Stereochemical Study of (±)-(2R*, 11bS*)-9,10-Dimethoxy-1,3,4,6,7,11b-hexahydrospiro[benzo[a]quinolizine-2,5’-oxazolidine]-2’,4’-dione

J. Carlos Menéndez, Mercedes Villacampa, 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*)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydrospiro[benzo[a]quinolizine-2,5’-oxazolidine]-2’,4’-dione (1) was achieved by two alternative route, involving the cyclization of α-hydroxy amide (5) with ethyl carbonate in the presence of sodium hydride or treatment of cyanohydrin (3) with chlorosulfonyl isocyanate followed by acid hydrolysis. The stereochemistry of 1 was established on the basis of a spectroscopic study of its precursor (6).