Corypalline

Corypalline, CnHijOjN (Corydalis spp. Nos. 9, 22 list, p. 170). This phenolic base, m.p. 168°, picrate, m.p. 178°, contains one methoxyl group and on methylation yields 2-methyl-6 7-dimethoxytetrahydrof5oquinoline, Ci2Hi,02N, m.p. 82°, and on ethylation, 2-methyl-6-methoxy-7-ethoxy-tetrahydrofsoquinoline, m.p. 65°, whence the free hydroxyl appears to be at C and this has been confirmed by the synthesis of corypalline by a method analogous with that used by Spath, Orekhov and Kuffner. Corypalline is therefore hydrohydrastinine (XII) with the methylenedioxy group replaced by MeO at C and. OH at C (Manske). ... [Pg.160]

Other simple naturally occurring methyltetrahydrofsoquinolines are hydrohydrastinine (XII), (p. 164) found, like corypalline, in Corydalis spp., and hydrocotarnine found in opium (p. 201). [Pg.160]

Nelumbium nelumbo Druce. Lian Zi Xin (Lotus) (plumule) Liensinine, isoliensinine, neferine, lotusine, methyl-corypalline, demethyl-coclaurine.33 Tranquilizing and antihypertensive. [Pg.115]

N.A. Thalictrum dasycarpum Fisch. Ave-Lall. T. occidental A. Gray Thalidasine, thalicarpine, thalisopavine, corypalline, norargemonine, trans-5, cw-9-octadecadienoic acid, dasycarponin, bis-norargemonine, L-laudanidine, tram -5 -hexadecenoic acid.302-333 A tumour inhibitor, relieve dizziness and ear problems. [Pg.304]

Methyl-corypalline Methyl eugenol Methyl isobutyl ketone Methyl isocupressate Methyl-l-propenyl disulfide Methyl-laurate Methyl-n-amyl ketone Methyl n-nonyl ketone Methyl nigakinone Methyl palmitate Methyl-pelletierine Methyl salicylate Methyl-swertianin Methylacetic acid Methylanthranilate Methylchavicol Methylcytisine... [Pg.454]

Corypalline (165 R = H)249 could be oxidatively dimerized electrochemi-cally in overall yields ranging from 44 to 85% depending on experimental conditions. Two types of dimers are obtained, the amount of carbon-carbon dimer 166 decreasing when R was varied from H through methyl to ethyl, and the product distribution shifted toward the carbon-oxygen-carbon dimer 167, presumably because of steric hindrance250 [Eq. (103)]. [Pg.300]

One of the most reliable electrochemical methods for the synthesis of alkaloidal skeletons is the oxidative coupling of phenolic and related compounds. A typical early example is the oxidative coupling of corypalline 1 to its dimer 2 ... [Pg.132]

The hydrastinine derivative (4) has been converted into the diol (5), which has been synthesized from the glycidic ester (6) via the diester (7)8,9 (Scheme 1). The dissociation constants of corypalline and isocorypalline in acetonitrile have been measured.10... [Pg.88]

Treatment of corypalline (13) with lead tetraacetate leads57 to the quinol acetate (14) which rearranges in acetic anhydride-sulfuric acid to yield the 4-acetoxytetrahydroisoquinoline (15). The reduction of the lactol (16) to 4-hydroxytetrahydroisoquinoline (17) has been reported.70... [Pg.115]

Since many isoquinoline alkaloids incorporate a guiacol moiety, we first tried to oxidize the most accessible 6-methoxy- and 7-methoxy-l,2,3,4-tetrahydroisoquinolinols (types A and B) with LTA. Later, tetrahydro-isoquinolinols of type C were also used. In spite of Wessely s statement (16) that LTA oxidation of both vanillin and isovanillin affords the corresponding o-quinol acetates, for a while we were able to obtain not the o-quinol acetate 2 from corypalline (1) but the p-quinol acetate 3 (17). At the outset of our study (IS), LTA oxidation of isocorypalline (4) gave no isolable o-quinol acetate 5, 4-acetoxyisocorypalline (6) being isolated instead. [Pg.70]

Isocorypal1ine (4, R =H, R =Me) has been oxidised by lead (IV) -acetate to the quinone acetal (5) which suffers Thiele acetylation to a product that may be hydrolysed and O-methylated to tehuanine (H. Hara et al.. Heterocycles, 1982, ]] (Special Issue), 293. Corypalline (4, R =Me, R =H) with lead tetra-... [Pg.261]

Doryanine, liriodenine, isocorydine, anonaine, reticuline, corypalline, doryphorine, doryflavine, choline chloride... [Pg.121]

Lemaireocereine has been isolated from Backebegia militaris and a new quaternary alkaloid, pycnarrhine, identified as 7-hydroxy-6-methoxy-2-methyl-3,4-dihydroisoquinolinium chloride, has been isolated from Pycnarrhena longifoliaCorypalline (1 R = H) has been oxidised by lead tetra-acetate to the dienone (2), which reacts with veratrole and with corypalline in the presence of trifluoro-... [Pg.122]

O-demethylation and reetherification or methylenation of the liberated phenolic groups (346-348). The alkaloid corypalline (lc) can be conveniently prepared from 6,7-dimethoxy-3,4-dihydroisoquinoline (349). The first step is partial demethylation of the methoxyl at C-7. It gives rise to the monomethoxy derivative which on hydrogenation affords corypalline (Scheme 1). [Pg.401]

Scheme 1. Transformation of 6,7-dimethoxy-3,4-dihydroisoquinoline into corypalline (1 iff (349).

Stock and Shia studied the dissociation constants of corypalline (lc) and isocorypalline in acetonitrile (386). [Pg.406]

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