Zur Konstitution des Chelidonins

Späth, Ernst; Kuffner, Friedrich

doi:10.1002/cber.19310640229

Cited by 30 publications

(11 citation statements)

References 2 publications

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“…[M]™ 348 (100), 333 (9), 318 (6), 307 (4), 290 (5), 167 (3), 154 (37), 136 (35), 124 (5). his,{6-(5.6-Dihydrocbelerythrinyl)} ether [3].-Chelerythrine chloride [lb] (59 mg) was dissolved in H20 and the solution was made alkaline with a saturated solution of K2C03.…”

Section: And Discussionmentioning

confidence: 99%

“…The solution was allowed to stand at room temperature. After two days, colorless crystals were collected and dried in vacuo (28 mg): mp 256-258°; ir (nujol) v max 1600 (aromatic C=C), 1495, 1405,1280,1235, 1195,1165,1140,1105, 1080, 1035 (C-O-C), 1015, 970, 940, 890, 860, 845, 820 cm™1; 'Hand 13C-nmr data (CDC13), see Table 1; 13H nmr (80 MHz, DMSO-¿6) 2.98 (3H, s, NMe), 2.36,3.67 (3H each, 2 X s, 2 XOMe), 6.21,6.24 (2H, OCH20), 6.41 (1H, s, H-6), 6.98-7.86 (6H, m, aromatic H); eims m/z [ -1]* 711 (0.3), 682 (0.1), 681 (0.4), 666 (0.2), 665 (0.5), 578 (0.07), 522 (0.1), 478 (0.1), 382 (0.3), 380 (1.3), 364 (3), 348 (100), 333 (66), 318(13), 304 (5), 290 (31), 275 (7), 232 (7), 217 (6), 188 (6), 166 (6); cims (positive-ion) m/z [M +1]+ 713(0.9), 433 (0.7), 378 (6), 362 (9), 350 (64), 348 (100), 333 (25); cims (negative-ion) m/z [M-H]~711 From the mother liquor, 33 mg of an unidentified substance with a mp of 111-113°c rystallized.…”

Section: And Discussionmentioning

confidence: 99%

“…The spectrum was recorded at 70°. In addition to the signals of -*H nmr(80MHz) 6.05 (2H, s, OCH20), 6.02 (1H, s, H-6), 4.00, 3.94, (3H each, 2Xs, 2XOMe), 2.72 (3H, s, NMe).…”

Section: Treatment Of Chelerythrine Chloridementioning

confidence: 99%

“…Although the structures of the quaternary cations la and lb have been well known since 1931 (6,7), the structures of the free bases have apparently not been completely elucidated until now.…”

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confidence: 99%

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Structure of Chelerythrine Base

Dostál¹,

Táborská²,

Slavík³

et al. 1995

J. Nat. Prod.

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The structure of chelerythrine free base was examined. When chelerythrine chloride [lb] was treated with aqueous K2CO} solution, bis[6-(5,6-dihydrochelerythrinyl)] ether[3] was obtained. An excess of aqueous ammonia under the same conditions yielded bis [6-(5,6-dihydrochelerythrinyl)] amine [4], The structures of both derivatives were determined by elemental analysis, ir, ID and 2D nmr, eims, and cims. The formation of an unstable hydroxy adduct 2a (pseudobase) was observed in 'H-nmr experiments only.

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Section: And Discussionmentioning

confidence: 99%

Section: And Discussionmentioning

confidence: 99%

“…The spectrum was recorded at 70°. In addition to the signals of -*H nmr(80MHz) 6.05 (2H, s, OCH20), 6.02 (1H, s, H-6), 4.00, 3.94, (3H each, 2Xs, 2XOMe), 2.72 (3H, s, NMe).…”

Section: Treatment Of Chelerythrine Chloridementioning

confidence: 99%

mentioning

confidence: 99%

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Structure of Chelerythrine Base

Dostál¹,

Táborská²,

Slavík³

et al. 1995

J. Nat. Prod.

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“…In oxyacanthine and curine (a component of the arrow poison curare), he recognized two compounds derived from benzylisoquinoline (4) [35]. He was able to characterize the main alkaloid of celandine, chelidonine (5) [36][37][38], as well as tazettine (6) [39] (a narcissus alkaloid) by structural formulas. In 1921, Späth and Erich Tschelnitz [40] reported the constitutional formula of the pyridine alkaloid ricinine (7), isolated like the extremely poisonous ricin from Ricinus communis (Fig.…”

Section: Ordinarius At the Iind Chemical Institutementioning

confidence: 99%

On the occasion of the 100th anniversary: Ernst Späth and his mescaline synthesis of 1919

Soukup

2019

Monatsh Chem

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Characterizing plant ingredients has been the main topic of chemical research at the University of Vienna since the beginning of the last half of the nineteenth century, especially at the IInd Chemical Institute (founded in 1870). The remarkable success in many fields of natural organic product structure elucidation was in part the result of the discovery of important identifying reactions of functional groups in organic molecules by Austrian chemists, e.g., Lieben´s iodoform test, the Herzig-Meyer´s method for the determination of methylamino groups or Zeisel´s method for the determination of methoxy groups in organic compounds. Ernst Späth was the most prominent exponent of the Viennese school of phytochemistry. He and his coworkers identified more than 120 phytochemical substances. His mescaline synthesis of 1919 has marked a milestone in the chemistry of organic natural products.

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Enantioselective Total Synthesis of (+)‐Homochelidonine by a Pd^II‐Catalyzed Asymmetric Ring‐Opening Reaction of a meso‐Azabicyclic Alkene with an Aryl Boronic Acid

2006

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Zur Konstitution des Chelidonins

Cited by 30 publications

References 2 publications

Structure of Chelerythrine Base

Structure of Chelerythrine Base

On the occasion of the 100th anniversary: Ernst Späth and his mescaline synthesis of 1919

Enantioselective Total Synthesis of (+)‐Homochelidonine by a Pd^II‐Catalyzed Asymmetric Ring‐Opening Reaction of a meso‐Azabicyclic Alkene with an Aryl Boronic Acid

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Zur Konstitution des Chelidonins

Cited by 30 publications

References 2 publications

Structure of Chelerythrine Base

Structure of Chelerythrine Base

On the occasion of the 100th anniversary: Ernst Späth and his mescaline synthesis of 1919

Enantioselective Total Synthesis of (+)‐Homochelidonine by a PdII‐Catalyzed Asymmetric Ring‐Opening Reaction of a meso‐Azabicyclic Alkene with an Aryl Boronic Acid

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Product

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Enantioselective Total Synthesis of (+)‐Homochelidonine by a Pd^II‐Catalyzed Asymmetric Ring‐Opening Reaction of a meso‐Azabicyclic Alkene with an Aryl Boronic Acid