First synthesis of the antimalarial naphthylisoquinoline alkaloid dioncophylline C, and its unnatural anti-HIV dimer, jozimine C1

Tetrahedron

Volumn 54, Issue 3-4, 1998, Pages 497-512

  Bringmann, Gerhard ^a   Holenz, Jörg ^a   Weirich, Ralf ^a   Rübenacker, Martin ^a   Funke, Christian ^a   Boyd, Michael R ^b   Gulakowski, Robert J ^b   François, Guido ^c  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b NATIONAL CANCER INSTITUTE   (United States)

^c INSTITUTE OF TROPICAL MEDICINE   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTIMALARIAL AGENT; DIMER; DIONCOPHYLLINE C; ISOQUINOLINE DERIVATIVE; JOZIMINE C; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0032518670     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10301-5     Document Type: Article

References (31)

1. 1. "Acetogenic Isoquinoline Alkaloids", part 105; for part 104, see Bringmann, G.; Holenz, J.; Aké Assi, L.; Hostettmann, K. Planta Med., submitted. - "Antiprotozoal Activity of Naphthylisoquinoline Alkaloids", part 10; for part 9, see ref. 6. - "HIV-Inhibitory Natural Products", part 44; for part 43, see Bokesch, H.; Young, S. M.; McKee, T. C.; Blunt, J. W.; Boyd, M. R. Nat. Prod. Lett., in press.
2. 1. "Acetogenic Isoquinoline Alkaloids", part 105; for part 104, see Bringmann, G.; Holenz, J.; Aké Assi, L.; Hostettmann, K. Planta Med., submitted. - "Antiprotozoal Activity of Naphthylisoquinoline Alkaloids", part 10; for part 9, see ref. 6. - "HIV-Inhibitory Natural Products", part 44; for part 43, see Bokesch, H.; Young, S. M.; McKee, T. C.; Blunt, J. W.; Boyd, M. R. Nat. Prod. Lett., in press.
3. 1. "Acetogenic Isoquinoline Alkaloids", part 105; for part 104, see Bringmann, G.; Holenz, J.; Aké Assi, L.; Hostettmann, K. Planta Med., submitted. - "Antiprotozoal Activity of Naphthylisoquinoline Alkaloids", part 10; for part 9, see ref. 6. - "HIV-Inhibitory Natural Products", part 44; for part 43, see Bokesch, H.; Young, S. M.; McKee, T. C.; Blunt, J. W.; Boyd, M. R. Nat. Prod. Lett., in press.
4. 1. "Acetogenic Isoquinoline Alkaloids", part 105; for part 104, see Bringmann, G.; Holenz, J.; Aké Assi, L.; Hostettmann, K. Planta Med., submitted. - "Antiprotozoal Activity of Naphthylisoquinoline Alkaloids", part 10; for part 9, see ref. 6. - "HIV-Inhibitory Natural Products", part 44; for part 43, see Bokesch, H.; Young, S. M.; McKee, T. C.; Blunt, J. W.; Boyd, M. R. Nat. Prod. Lett., in press.
5. 2. Bringmann, G.; Rübenacker, M.; Weirich, R.; Aké Assi, L. Phytochemistry 1992, 31, 4019-4024.
6. 3. Bringmann, G.; Pokorny, F. in The Alkaloids; Cordell, G. ed.; Academic Press: New York, Vol. 46, 1995, pp. 127-271.
7. 4. François, G.; Timperman, G.; Holenz, J.; Aké Assi, L.; Geuder, T.; Maes, L.; Dubois, J.; Hanocq, M.; Bringmann, G. Ann. Trop. Med. Parasitol. 1996, 90, 115-123.
8. 5. François, G.; Bringmann, G.; Dochez, C.; Schneider, C.; Timperman, G.; Aké Assi, L. J. Ethnopharmacol. 1995, 46, 115-120.
9. 6. François, G.; Timperman, G.; Aké Assi, L.; Eling, W.; Holenz, J.; Bringmann, G. Antimicrob. Agents Chemother., in press.
10. 7. Bringmann, G.; Saeb, W.; Koppler, D.; François, G. Tetrahedron 1996, 52, 13409-13418.
11. 8. Bringmann, G.; Rübenacker, M.; Jansen, J. R.; Scheutzow, D.; Aké Assi, L. Tetrahedron Lett. 1990, 31, 639-642.
12. 9. Bringmann, G.; Jansen, J. R.; Reuscher, H.; Rübenacker, M.; Peters, K.; von Schnering, H. G. Tetrahedron Lett. 1990, 31, 643-642.
13. 10. Bringmann, G. Bull. Soc. Chim. Belg. 1996, 105, 601-603.
14. 11. Bringmann, G.; Götz, R.; François, G. Tetrahedron 1996, 52, 13419-13426.
15. 12. Boyd, M. R.; Hallock, Y. F.; Cardellina II, J. H.; Manfredi, K. P.; Blunt, J. W.; McMahon J. B.; Buckheit Jr., R. W.; Bringmann, G.; Schäffer, M.; Cragg, G. M.; Thomas, D. W.; Jato, J. G. J. Med. Chem. 1994, 37, 1740-1745.
16. 13. Hallock, Y. H.; Manfredi, K. P.; Blunt, J. W.; Cardellina II, J. H.; Schäffer, M.; Gulden, K.-P.; Bringmann, G.; Lee, A. Y.; Clardy, J.; François, G. J. Org. Chem. 1994, 59, 6349-6355.
17. 14. Gable, R. W.; Martin, R. L.; Rizzacasa, M. A. Aust. J. Chem. 1995, 48, 2013-2021.
18. 15. Bringmann, G.; Jansen, J. R.; Rink, H.-P. Angew. Chem. 1986, 98, 917-919; Angew. Chem. Int. Ed. Engl. 1986, 25, 913-915.
19. 15. Bringmann, G.; Jansen, J. R.; Rink, H.-P. Angew. Chem. 1986, 98, 917-919; Angew. Chem. Int. Ed. Engl. 1986, 25, 913-915.
20. 16. Bringmann, G., Harmsen, S.; Schupp, O.; Walter, R. in Metal Assisted 'Twisting' of Axes: A Novel Approach to Stereoselective Biaryl Synthesis; Werner, H., Sundermeyer, J. eds.; Vieweg: Braunschweig, 1995, pp. 137-142.
21. 17. Bringmann, G.; Götz, R. Harmsen, S.; Holenz, J.; Walter, R. Liebigs Ann. 1996, 2045-2058.
22. 18. Bringmann, G.; Weirich, R.; Reuscher, H.; Jansen, J. R.; Kinzinger, L.; Ortmann, T. Liebigs Ann. Chem. 1993, 877-888.
23. 19. By the use of an N-trifluoroacetyl instead of the N-benzyl group, an atropo-diastereomeric ratio of >95:5 is obtained, similar to previous experience in the ancistrocladine synthesis.3
24. 20. Bringmann, G.; Schneider, S. Synthesis 1983, 139-141.
25. 21. Despite its close structural similarity to korupensamines A (2a) and B (2b), the 'monomeric halves' of michellamine B, dioncophylline C (1) was not coupled by the highly substrate specific dimerization enzyme recently isolated from various Ancistrocladus species and even from T. peltatum: Schlauer, J., Wiesen, B., Rückert, M., Aké Assi, L., Haller, R. D., Bär, S., Fröhlich, K.-U., Bringmann, G. Arch. Biochem. Biophys., in press.
26. 22. Bringmann G.; Harmsen, S.; Holenz, J.; Geuder, T.; Götz, R.; Keller, P. A.; Walter, R. Hallock, Y. F.; Cardellina II, J. H.; Boyd, M. R. Tetrahedron 1994, 50, 9643-9648.
27. 23. This is corroborated by spectroscopic hints at the presence of another regioisomeric product, although in small amounts.
28. 24. Even by directed search, jozimine C (4) has not yet been found in dioncophylline C producing material of T. peltatum.
29. 25. Tiecco, M. Synthesis 1988, 749-592.
30. 26. Vlietstra, E. J.; Zwikker, J. W.; Nolte, R. J. M.; Drenth, W. J. R. Neth. Chem. Soc. 1982, 101, 460-462.
31. 27. Gulakowski, R. J.; McMahon, J. B.; Staley, P. G.; Moran, R. A.; Boyd, M. R. J. Virol. Methods 1991, 33, 87-100.