Studies on the Alkaloids of Fumariaceos Plants. X. : Alkaloids of Corydalis platycarpa MAKINO. (1)

Tani, Chiaki; Imanishi, Isamu; Nishijo, Juziro

doi:10.1248/yakushi1947.90.3_407

Cited by 5 publications

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“…The organic layer was dried (Na 2 SO 4 ) and concentrated to give an oil (36 mg), which was crystallized from MeOH-Et 2 O to give 4a (31 mg, 87%), mp 150−151 °C (lit . mp 145−146 °C; − 147 °C; 148 °C; 148−150 °C; 149.5−150.5 °C;48h 150−151 °C; 151−151.5 °C). The 1 H NMR spectrum of this sample was identical with the reported data. ,,, …”

Section: Methodsmentioning

confidence: 99%

“…mp 145−146 °C; − 147 °C; 148 °C; 148−150 °C; 149.5−150.5 °C;48h 150−151 °C; 151−151.5 °C). The 1 H NMR spectrum of this sample was identical with the reported data. ,,, …”

Section: Methodsmentioning

confidence: 99%

“…The 1 H NMR spectrum of this sample was identical with the reported data. 78,81,82,85 (()-Sinactine (4b): 90% yield; mp 168-170 °C (MeOH) (lit. 86 46,48i,89 (()-Stylopine (4d): 86% yield: mp 211-214 °C (MeOH) (lit.…”

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confidence: 99%

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Synthesis of Phthalideisoquinoline and Protoberberine Alkaloids and Indolo[2,1-a]isoquinolines in a Divergent Route Involving Palladium(0)-Catalyzed Carbonylation¹

et al. 1999

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6,7,3',4'-Alkoxy-substituted 1-(2'-bromobenzoyl)-3,4-dihydroisoquinoline methiodides 17 were treated with sodium borohydride in methanol or acetic acid to give erythro-1-(2'-bromo-alpha-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinolines 19. Treatment of 17 with lithium aluminum hydride in tetrahydrofuran gave the threo-isomer 20 in preference to the erythro 19. On the basis of studies on palladium(0)-catalyzed carbonylation of 2-bromo-3,4-dimethoxybenzyl alcohol to 6,7-dimethoxyphthalide, amino alcohol 19 or 20 was treated with a catalytic amount of palladium(II) acetate and triphenylphosphine in an atmosphere of carbon monoxide in the presence of chlorotrimethylsilane and potassium carbonate in boiling toluene to give the corresponding erythro- or threo-types of phthalideisoquinoline alkaloids 1 or 2, respectively. One-pot cyclization of the erythro-amino alcohols 19 was achieved by heating in N,N-dimethylformamide containing potassium carbonate to give 2,3,8,9- or 2,3,9,10-alkoxy-substituted 5,6-dihydroindolo[2,1-a]isoquinolines 3, which have a unique tetracyclic skeleton characteristic of dibenzopyrrocoline alkaloids. Similarly, palladium(0)-catalyzed carbonylation of 1-(2'-bromobenzyl)tetrahydroisoquinolines 21 in the presence of excess potassium carbonate was found to give 8-oxoberbines 22, which on reduction with lithium aluminum hydride can be converted to protoberberine alkaloids 4.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis of Phthalideisoquinoline and Protoberberine Alkaloids and Indolo[2,1-a]isoquinolines in a Divergent Route Involving Palladium(0)-Catalyzed Carbonylation¹

et al. 1999

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Capillary electrophoresis of tetrahydroberberine alkaloids: chiral separation by cyclodextrin-modified micellar electrokinetic chromatography

et al. 1999

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Systematic review of the alkaloid constituents in several important medicinal plants of the Genus Corydalis

et al. 2021

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Studies on the Alkaloids of Fumariaceos Plants. X. : Alkaloids of Corydalis platycarpa MAKINO. (1)

Cited by 5 publications

References 0 publications

Synthesis of Phthalideisoquinoline and Protoberberine Alkaloids and Indolo[2,1-a]isoquinolines in a Divergent Route Involving Palladium(0)-Catalyzed Carbonylation¹

Synthesis of Phthalideisoquinoline and Protoberberine Alkaloids and Indolo[2,1-a]isoquinolines in a Divergent Route Involving Palladium(0)-Catalyzed Carbonylation¹

Capillary electrophoresis of tetrahydroberberine alkaloids: chiral separation by cyclodextrin-modified micellar electrokinetic chromatography

Systematic review of the alkaloid constituents in several important medicinal plants of the Genus Corydalis

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Studies on the Alkaloids of Fumariaceos Plants. X. : Alkaloids of Corydalis platycarpa MAKINO. (1)

Cited by 5 publications

References 0 publications

Synthesis of Phthalideisoquinoline and Protoberberine Alkaloids and Indolo[2,1-a]isoquinolines in a Divergent Route Involving Palladium(0)-Catalyzed Carbonylation1

Synthesis of Phthalideisoquinoline and Protoberberine Alkaloids and Indolo[2,1-a]isoquinolines in a Divergent Route Involving Palladium(0)-Catalyzed Carbonylation1

Capillary electrophoresis of tetrahydroberberine alkaloids: chiral separation by cyclodextrin-modified micellar electrokinetic chromatography

Systematic review of the alkaloid constituents in several important medicinal plants of the Genus Corydalis

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Synthesis of Phthalideisoquinoline and Protoberberine Alkaloids and Indolo[2,1-a]isoquinolines in a Divergent Route Involving Palladium(0)-Catalyzed Carbonylation¹

Synthesis of Phthalideisoquinoline and Protoberberine Alkaloids and Indolo[2,1-a]isoquinolines in a Divergent Route Involving Palladium(0)-Catalyzed Carbonylation¹