D-corydaline

Corydalis yanhusuo W. T. Wang ex Z. Y. Su et C. Y. Wu China d-corydaline, corydalis, dl-tetrahydropalmatine, crybulbine, alpha-allocryptopine, tetrahydrocoptisine, corydalamine, tetrahydrocolumbamine, protopine, coptisine, dehydrocorydaline, columbamine, dehydrocorydalmine.33 Overdosage is toxic. Analgesic, sedative, hypnotic, synergistic, increase coronary flow. 

In the course of work leading to the elucidation of the structure of corydaline at the time that these researches were undertaken the structures of none of the protoberberines were known, and most of this work is of historical interest only. Had the later work on berberine and tetrahydro-palmatine been available the determination of the structure of corydaline would have been an easy task. That it contains the same nuclear structure is indicated by its ready oxidation to dehydrocorydaline. Unlike the reduction of palmatine which gives a single product, the dl-tetrahydro base, the reduction of dehydrocorydaline gives rise to a mixture of meso-and racemic corydaline (245). The mesocorydaline has been resolved by means of d-camphorsulfonic acid, but the d-base is not identical with d-corydaline. It is obvious therefore that corydaline contains two asymmetric carbons. 

Papaverine was condensed with formaldehyde to methylenepapaverine (XXII), which on successive catalytic and electrolytic hydrogenation yielded two dl-methyltetrahydropapaverines (XXIII), which on successive demethylation, condensation with formaldehyde and re-methylation yielded a mixture of bases, from which the two optically inactive corydalines (XXIV), wic ocorydaline, m.p. 168-4 (vac.), and d/-corydaline, m.p. 132—3°, identical with the products obtained by the hydrogenation of dehydrocorydaline were isolated. For the conversion of corycavine to corydaline, see p. 304. 

Dehydrocorydaline eontains four methoxyl groups. On reduetion it furnishes two stereoisomerides of eorydaline, m.p. 135°, and m.p. 158-9° (163-4° vac.), Spath) the latter ( 2f.9oeorydaline) by erj stallisation of the d-eamphorsulphonate can be partially separated into d- and Z-forms, the d-form of which is not identical with natural corydaline.The second isomeridc, m.p. 135°, has not been resolved into optically active components, but from the sulphonic acid the Z-compoiient has been isolated by crystallisation of the brucine salt, and this is taken to indicate that the inactive corydaline, m.p. 135°, is dZ-corydaliiie. °... 

C alkylation was used in the corydaline synthesis 194). LukeS and Dedek 195) obtained on methylation of l-methyl-2-ethylidenepyrrolidine a C-alkylation product, i.e., l-methyl-2-isopropyl-/l -pyrroline (106). Alkylation of the same enamine with ethyl bromoacetate was the first synthetic step in the preparation of D,L-pseudoheliotridane 196). 

Corydaline has only been found in the d-form, which melts at 136°. It is readily soluble in choroform, moderately so in ether, and sparingly in... 

C. solida (L.) Swartz. Protopine, allocryptopine, d stylopine, d- and dZ-tetrahydropalmatine, d-canadine, aurotensine, corydaline, 22, 23... 

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