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Paper | Regular issue | Vol 31, No. 2, 1990, pp.353-366
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5250
Preparation of Enatiomerically Pure Decahydro-6H-isoquino[2,1-g][1,6]naphthyridines Utilizing the Openshaw-Whittaker Hexahydrobenzo[a]quinolizinone Resolution.

Robin D. Clark,* John R. Kern, Lilia J. Kurz, and Janis T. Nelson

*Institute of Organic Chemistry, Syntex Research, Palo Alto, California 94304, U.S.A.


The (8aR,12aS,13aS)-decahydro-6H-isoquino[2,1-g][1,6]naphthyridine sulfonamides 1a,b were prepard from (+)-(3R,11bS)-3-cyanoethylhexahydrobenzo[a]quinolizinones 3a,b. These key intermediates were obtained by resolution of (±)-3a,b with (+)-camphorsulfonic acid in ethyl acetate accroding the the conditions used in the Openshaw-Whittaker synthesis of (-)-emitine.