Monomeric naphthylisoquinoline alkaloids and synthesis methods t

Details Monomeric naphthylisoquinoline alkaloids and synthesis methods t Monomeric naphthylisoquinoline alkaloids and synthesis methods t

1996-07-01

1998-06-09

Davis, Zinna Northington

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546141, 546149, C07D21702

Patent

active

057636133

ABSTRACT:
The present invention provides methods of preparing monomeric naphthylisoquinoline alkaloids, including the antiparasitic korupensamines and related compounds, as well as non-korupensamines and other monomeric naphthylisoquinoline alkaloids. The invention also provides new, medically useful naphthylisoquinoline compounds and derivatives thereof.

REFERENCES:
patent: 5260315 (1993-11-01), Bringmann et al.
patent: 5409938 (1995-04-01), Boyd
Govindachari et al, Tetrahedron, vol. 27, 1971 pp. 1013-1026.
Govidachari et al, Indian J. Chem, vol. 13, No. 7, pp. 641-643, 1975.
Foucher, Plant. Med. Phytother., vol. 9, No. 9 pp. 87-98, 1975.
Boyd et al., "Anti-HIV Michellamines from Ancistrocladus korupensis," J. Medicinal Chemistry, 37(12), 1740-1745 (1994).
Bringmann, The Alkaloids, 29 (Brossi, ed.), Academic Press, New York, 1986, pp. 141-184.
Bringmann et al., "Regioselective and Atroposiomeric-Selective Aryl Coupling to Give Naphthyl Isoquinoline Alkaloids: The First Total Synthesis of (--)-Ancistrocladine," Angew. Chem. Int. Ed. Engl., 25(10), 913-915 (1986).
Bringmann et al., "Atropdiastereoselective Ring Opening of Bridged, `Axial-Prostereogenic` Biaryls: Directed Synthesis of (+)-Ancistrocladisine," Angew. Chem. Int. Ed. Engl., 28(12), 1672-1673 (1989).
Bringmann et al., "Chiral Economy with Respect to Rotational Isomerism: Rational Synthesis of Hamatine and (Optionally) Ancistrocladine from Joint Helical Precursors," Heterocycles, 28(1), 137-142 (1989).
Bringmann et al., "The Synthesis of All Possible Isomeric 6, 8-Dioxygenated 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinoline Methyl Ethers--Useful Chiral Building Blocks for Naphthylisoquinoline Alkaloids," Liebigs Ann, Chem,877-888 (1993).
Bringmann et al., "Atrop-diastereomer Separation by Racemate Resolution Techniques: N-Methyl-Dioncophylline A and its 7-Epimer from Ancistocladus abbreviatus," Phytochemistry, 30(4), 1307-1310 (1991).
Bringmann et al., "Dioncopeltine A and Dioncolactone A: Alkaloids from Triphyophyllum peltatum," Phytochemistry, 30(5), 1691-1696 (1991).
Bringmann et al., "Dioncophylline B, A Naphthylisoquinoline Alkaloid with A New Coupling Type from Triphyophyllum peltatum," Phytochemistry, 30(11), 3845-3847 (1991).
Bringmann et al., "Ancistrobrevine B, The First Naphthylisoquinoline Alkaloid with a 5,8'-Coupling Site, and Related Compounds from Ancistrocladus abbreviatus," Phytochemistry, 31(11), 4011-4014 (1992).
Bringmann et al., "(+) -Dioncophyllacine A, A Naphthylisoquinoline Alkaloid with a 4-Methoxy Substituent from the Leaves of Triphyophyllum peltatum," Phytochemistry, 31(11), 4015-4108 (1992).
Bringmann et al., "Dioncophylline C from the Roots of Triphyophyllum peltatum, the First 5,1'-Coupled Dioncophyllaceae Alkaloid," Phytochemistry, 31(11), 4019-4024 (1992).
Bringmann et al., "On the Biosynthesis of Acetogenic Tetrahydroisoquinoline Alkaloids: First In Vivo Feeding Experiments," Planta Med., 57 (Suppl. 2), A98 (1991).
Bringmann et al., "Ancistrobrevine D: An Unusual Alkaloid from Ancistocladus abbreviatus," Planta Med., 58 (Suppl. 1), A703-704 (1992).
Bringmann et al., "A New Atropisomeric Dioncophylline A Derivative from Triphyophyllum peltatum," Planta Med., 59 (Suppl.), A621-622 (1993).
Bringmann et al., "The Cultivation of Tropical Lianas of the Genus Ancistrocladus," Planta Med., 59 (Suppl.), A623-624 (1993).
Bringmann et al., "Improved Methods for Dehydration and Hydroxy/Halogen Exchange Using Novel Combinations of Triphenylphosphine and Halogenated Ethanes," Synthesis, 139-141 (1983).
Bringmann et al., "Stereocontrolled Ring Opening of Axially Prostereogenic Biaryl Lactones with Hydrogen Nucleophiles: Directed Synthesis of a Dioncophylline A Precursor and (Optionally) its Atropdiastereomer," Synthesis, 825-827 (1991).
Bringmann et al., "On the Structure of the Dioncophyllaceae Alkaloids Dioncophylline A (`Triphyophylline`) and `O-Methyl-Triphyophylline,`" Tetrahedron Letters, 31(5), 639-642 (1990).
Bringmann et al., "First Total Synthesis of (-)-Dioncophylline A (`Triphyophylline`) and of Selected Stereoisomers: Complete (Revised) Stereostructure," Tetrahedron Letters, 31(5), 643-646 (1990).
Fleischhauer e al., "Messung und Berechnung der CD-Sperktren der Biaryl-Alkaloide Ancistrocladein und Dioncophyllein A," Z. Naturforsch, 48b, 140-148 (1993).
Fran.cedilla.ois et al., "Activity of Extracts and Naphthylisoquinoline Alkaloids from Triphyophyllum peltatum, Ancistocladus abbreviatus and A. barteri against Plasmodium falciparum In Vitro," Phytochemistry, 35(6), 1461-1464 (1994).
Handford et al., "Syntheses of Eleutherolic Acid," J. Chem. Soc. , 3896-3897 (1963).
Owton et al., "tert-Butyl-3-Carboxyethyl-3-Phosphondiethylpropionate. A Novel Reagent for Stobbe-like Condensations," Synthetic Communications, 23(15), 2119-2125 (1993).
Rizzacasa et al., "Synthetic Approaches to the Alkaloids of the Acistrocladacea: Dehydroancistrocladisine," J. Chem. Soc., 301-302 (1989).
Thomas et al., "Ancistrocladus korupensis (Ancistrocladaceae): A New Species of Liana from Cameroon," Novon, 3(4), 494-498 (1993).
Bringmann et al., "First total synthesis of Korupensamines A and B," Heterocycles, 39(2), 503-508 (1994).
Bringmann et al., "Biomimetic oxidative dimerization of korupensamine A: Completion of the first total synthesis of michellamines A, B, and C" Tetrahedron, 50(32), 9643-9648 (1994).
Hoye et al., "Total synthesis of michellamines A-C: Important anti-HIV agents," Tetrahedron Letters, 35(47), 8747-8750 (1994).
Kelly et al., "Convergent total synthesis of the michellamines," Tetrahedron Letters, 35(41), 7621-7624 (1994).
Manfredi et al., "Novel alkaloids from the tropical plant Ancistrocladus abbreviatus inhibit cell killing by HIV-1 and HIV-2," Journal of Med. Chem., 34(12), 3402-3405 (1991).

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