THE ALKALOIDS OF FUMARIACEOUS PLANTS: XIV. CORYPALLINE, CORLUMIDINE AND THEIR CONSTITUTIONS

Abstract

Corypalline, C11H15O2N, a new phenolic alkaloid from Corydalis pallida and from the seeds of C. aurea, on methylation yielded the known 2-methyl-6:7-dimethoxy-tetrahydro-isoquinoline. On ethylation it yielded 2-methyl-6-methoxy-7-ethoxy-tetrahydro-isoquinoline identical with a specimen synthesized for purposes of comparison. Corypalline therefore is 2-methyl-6-methoxy-7-hydroxy-tetrahydro-isoquinoline, a synthesis of which was achieved.Oxidative fission of corlumidine O-ethyl ether yielded a base identical with a synthetic specimen of 1-hydroxy-2-methyl-6-methoxy-7-ethoxy-tetrahydro-isoquinoline. Treatment of the degradative as well as the synthetic base with alkali yielded the corresponding 1-keto-isoquinoline. Corlumidine therefore is 7-O-desmethyl-corlumine.Syntheses of 2-methyl-6-ethoxy-7-methoxy-tetrahydro-isoquinoline and the corresponding 1-keto-derivative are described.