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Two Atropisomeric N-Methyldioncophyllines A and N-Methylphylline, their Naphthalene-Free Heterocyclic Moiety, from Ancistrocladus barteri

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Veröffentlicht/Copyright: 2. Juni 2014
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Zeitschrift für Naturforschung B
Aus der Zeitschrift Zeitschrift für Naturforschung B Band 58 Heft 6

The West African plant Ancistrocladus barteri (Ancistrocladaceae) was investigated chemically for the first time. Besides the known naphthylisoquinoline alkaloids N-methyldioncophylline A and 7-epi-N-methyldioncophylline A (i.e. its atropo-diastereomer), a new naphthalene-free alkaloid, belonging to the ‘Dioncophyllaceae type’, was isolated. Its structure was elucidated by spectroscopic and degradative methods and confirmed by total synthesis. The new compound, named N-methylphylline, is exactly the isoquinoline “half” of both, N-methyldioncophylline A and its atropisomer. Furthermore, the related tetrahydroisoquinoline O,N-dimethylphylline, an intermediate in the chemical synthesis of N-methylphylline, was detected as a new natural product in crude extracts of A. barteri.

Keywords: Structural Elucidation; Naphthylisoquinoline Alkaloids; Ancistrocladaceae; Crystal Structure
Received: 2003-1-7
Published Online: 2014-6-2
Published in Print: 2003-6-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Artikel in diesem Heft

  1. Magnetic Properties of Compounds RE2Cu2Mg (RE = Y, La, Pr, Nd)
  2. Magnetic and Spectroscopic Properties of LiAuSn
  3. Synthesis, Characterization, Crystal Structure and Magnetic Properties of [(en)CuII(ImH)2](ClO4)2 (en = Ethylenediamine, ImH = Imidazole): A Metalloligand as a Building Block for Heterometal Chains
  4. Synthese und Struktur des Ammoniumsesquicarbonat Monohydrates (NH4)4[H2(CO3)3] ·H2O
  5. Ruthenocene mit sterisch anspruchsvollen Cyclopentadienylliganden
  6. R2Sn3 (R = La – Nd, Sm): A Family of Intermetallic Compounds with their Own Triclinic Structure
  7. The Synthesis and Structure of the Two Hexafluorophosphate Salts {Cu[P(C7H7)3](CH3CN)2}PF6 and {Cu[P(C7H7)3]2}PF6 Containing the Ligand Tri(1-cyclohepta-2,4,6-trienyl)phosphane
  8. Semi-Hydrogenated, Asymmetric Metallocene Catalysts for the Propylene Polymerization
  9. Crystal Structures of Heteronuclear Nickel(II)/Zinc(II) Doubly Oxygen Bridged Schiff-Base Complexes
  10. Hydroboration of Bis(trimethylsilylethynyl)silanes with 9-Borabicyclo[3.3.1]nonane. A New Route to 1-Sila-3-cyclopentenes and to a 1-Sila-2,4-cyclopentadiene
  11. Manganiophosphonium-Salze: Synthese, Eigenschaften und Struktur von Komplexen des Typs [CpMn(CO)(NO)PPh2H]BF4 und [Cp′Mn(CO)(NO)PPh2R]X (R = H, CH3, {CpMn(CO)(NO)}; X = BF4, PF6)
  12. Electrochemistry of Acetate-, Carbonate-, Sulfate-, and Dihydrogenphosphate-Bridged Dirhodium(II) Complexes
  13. Synthesis, Crystal and Magnetic Structure of the New Double Perovskite Ba2MnMoO6
  14. Two Atropisomeric N-Methyldioncophyllines A and N-Methylphylline, their Naphthalene-Free Heterocyclic Moiety, from Ancistrocladus barteri
  15. Darstellung von 2,3,8-substituierten Perhydrooxazolo[3,2-a]pyridinen und die Kristallstruktur von (E)-3-(2-Fluorbenzyliden)-1-[1,2-bis(2-fluorphenyl)- 2-hydroxyethyl]-3,4,5,6-tetrahydropyridiniumchlorid
  16. Teilweise Sauerstoff-Wanderung in der photochemischen Wolff-Umlagerung – α-Oxocarben-Oxiren-Isomerisierung oder intermolekularer Mechanismus?
https://doi.org/10.1515/znb-2003-0614
Schlagwörter für diesen Artikel
Structural Elucidation; Naphthylisoquinoline Alkaloids; Ancistrocladaceae; Crystal Structure

Artikel in diesem Heft

  1. Magnetic Properties of Compounds RE2Cu2Mg (RE = Y, La, Pr, Nd)
  2. Magnetic and Spectroscopic Properties of LiAuSn
  3. Synthesis, Characterization, Crystal Structure and Magnetic Properties of [(en)CuII(ImH)2](ClO4)2 (en = Ethylenediamine, ImH = Imidazole): A Metalloligand as a Building Block for Heterometal Chains
  4. Synthese und Struktur des Ammoniumsesquicarbonat Monohydrates (NH4)4[H2(CO3)3] ·H2O
  5. Ruthenocene mit sterisch anspruchsvollen Cyclopentadienylliganden
  6. R2Sn3 (R = La – Nd, Sm): A Family of Intermetallic Compounds with their Own Triclinic Structure
  7. The Synthesis and Structure of the Two Hexafluorophosphate Salts {Cu[P(C7H7)3](CH3CN)2}PF6 and {Cu[P(C7H7)3]2}PF6 Containing the Ligand Tri(1-cyclohepta-2,4,6-trienyl)phosphane
  8. Semi-Hydrogenated, Asymmetric Metallocene Catalysts for the Propylene Polymerization
  9. Crystal Structures of Heteronuclear Nickel(II)/Zinc(II) Doubly Oxygen Bridged Schiff-Base Complexes
  10. Hydroboration of Bis(trimethylsilylethynyl)silanes with 9-Borabicyclo[3.3.1]nonane. A New Route to 1-Sila-3-cyclopentenes and to a 1-Sila-2,4-cyclopentadiene
  11. Manganiophosphonium-Salze: Synthese, Eigenschaften und Struktur von Komplexen des Typs [CpMn(CO)(NO)PPh2H]BF4 und [Cp′Mn(CO)(NO)PPh2R]X (R = H, CH3, {CpMn(CO)(NO)}; X = BF4, PF6)
  12. Electrochemistry of Acetate-, Carbonate-, Sulfate-, and Dihydrogenphosphate-Bridged Dirhodium(II) Complexes
  13. Synthesis, Crystal and Magnetic Structure of the New Double Perovskite Ba2MnMoO6
  14. Two Atropisomeric N-Methyldioncophyllines A and N-Methylphylline, their Naphthalene-Free Heterocyclic Moiety, from Ancistrocladus barteri
  15. Darstellung von 2,3,8-substituierten Perhydrooxazolo[3,2-a]pyridinen und die Kristallstruktur von (E)-3-(2-Fluorbenzyliden)-1-[1,2-bis(2-fluorphenyl)- 2-hydroxyethyl]-3,4,5,6-tetrahydropyridiniumchlorid
  16. Teilweise Sauerstoff-Wanderung in der photochemischen Wolff-Umlagerung – α-Oxocarben-Oxiren-Isomerisierung oder intermolekularer Mechanismus?
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