First atropo-divergent total synthesis of the antimalarial korupensamines A and B by the 'lactone method'

Journal of Organic Chemistry

Volumn 65, Issue 7, 2000, Pages 2069-2077

  Bringmann, Gerhard ^a   Ochse, Michael ^a   Götz, Roland ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; KORUPENSAMINE A; KORUPENSAMINE B; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

ANTIMALARIALS; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ISOQUINOLINES; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; NAPHTHALENES; PALLADIUM; PLANTS, MEDICINAL; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 0034616313     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991634v     Document Type: Article

References (69)

1. Manfredi, K. P.; Blunt, J. W.; Cardellina, J. H., II; McMahon, J. B.; Pannell, L. K.; Cragg, G. M.; Boyd, M. R. J. Med. Chem. 1991, 34, 3402.
2. Boyd, M. R.; Hallock, Y. F.; Cardellina, J. H., II; Manfredi, K. P.; Blunt, J. W.; McMahon, J. B.; Buckheit, R. W., Jr.; Bringmann, G.; Schäffer, M.; Cragg, G. M.; Thomas, D. W.; Jato, J. G. J. Med. Chem. 1994, 37, 1740.
3. Hallock, Y. F.; Manfredi, K. P.; Blunt, J. W.; Cardellina, J. H., II; Schäffer, M.; Gulden, K.-P.; Bringmann, G.; Lee, A. Y.; Clardy, J.; François, G.; Boyd, M. R. J. Org. Chem. 1994, 59, 6349.
4. Hallock, Y. F.; Manfredi, K. P.; Dai, J.-R.; Cardellina, J. H., II; Gulakowski, R. J.; McMahon, J. B.; Schäffer, M.; Stahl, M.; Gulden, K.-P.; Bringmann, G.; François, G.; Boyd, M. R. J. Nat. Prod. 1997, 60, 677.
5. Hallock, Y. F.; Cardellina, J. H., II; Schäffer, M.; Stahl, M.; Bringmann, G.; François, G.; Boyd, M. R. Tetrahedron 1997, 53, 8121.
6. Hallock, Y. F.; Cardellina, J. H., II; Schäffer, M.; Bringmann, G.; François, G.; Boyd, M. R. Bioorg. Med. Chem. Lett. 1998, 8, 1729.
7. (a) Bringmann, G.; Feineis, D. Act. Chim. Thérapeut. 2000, 26, 151.
8. (b) Bringmann, G. In Guidelines and issue for the discovery and drug development against Tropical Diseases; Vial, H., Fairlamb, A., Ridley, R., Eds.; World Health Organisation: Geneva, in press.
9. Bringmann, G.; Götz, R.; Harmsen, S.; Holenz, J.; Walter, R. Liebigs Ann. 1996, 2045.
10. Schlauer, J.; Rückert, M.; Wiesen, B.; Herderich, M.; Aké Assi, L.; Haller, R. D.; Bär, S.; Fröhlich, K.-U.; Bringmann, G. Arch. Biochem. Biophys. 1998, 350, 87.
11. Bringmann, G.; Zagst, R.; Schäffer, M.; Hallock, Y. F.; Cardellina, J. H., II; Boyd, M. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1190.
12. Anon. J. Nat. Prod. 1992, 55, 1018.
13. Bringmann, G.; Götz, R.; Keller, P. A.; Walter, R.; Henschel, P.; Schäffer, M.; Stäblein, M.; Kelly, T. R.; Boyd, M. R. Heterocycles 1994, 39, 503.
14. (a) Hoye, T. R.; Mi, L. Tetrahedron Lett. 1996, 37, 3097.
15. (b) For an excellent brand-new full paper, see Hoye, T. R.; Chen, M.; Hoang, B.; Mi, L.; Priest, O. P. J. Org. Chem. 1999, 64, 7184.
16. Kelly, T. R.; Garcia, A.; Lang, F.; Walsh, J. J.; Bhaskar, K. V.; Boyd, M. R.; Götz, R.; Keller, P. A.; Walter, R.; Bringmann, G. Tetrahedron Lett. 1994, 35, 7621.
17. Bringmann, G.; Götz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, K. V.; Kelly, T. R. J. Org. Chem. 1998, 63, 1090.
18. Hobbs, P. D.; Upender, V.; Liu, J.; Pollart, D. J.; Thomas, D. W.; Dawson, M. I. J. Chem. Soc., Chem. Commun. 1996, 923.
19. Hoye, T. R.; Chen, M.; Mi, L.; Priest, O. P. Tetrahedron Lett. 1994, 35, 8747.
20. (a) Bringmann, G. Bull. Soc. Chim. Belg. 1996, 105, 601.
21. (b) Rizzacasa, M. A. In Studies in Natural Product Synthesis, Structure and Chemistry (Part F); Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1998; Vol. 20, pp 407-453.
22. Bringmann, G.; Saeb, W.; Koppler, D.; François, G. Tetrahedron 1996, 52, 13409.
23. Bringmann, G.; Holenz, J.; Weirich, R.; Rübenacker, M.; Funke, C.; Boyd, M. R.; Gulakowski, R. J.; François, G. Tetrahedron 1998, 54, 497.
24. Bringmann, G.; Götz, R.; François, G. Tetrahedron 1996, 52, 13419.
25. Upender, V.; Pollart, D. J.; Liu, J.; Hobbs, P. D.; Olsen, C.; Chao, W.; Bowden, B.; Crase, J. L.; Thomas, D. W.; Pandey, A.; Lawson, J. A.; Dawson, M. I. J. Heterocycl. Chem. 1996, 33, 1371.
26. Zhang, H.; Zembower, D. E.; Chen, Z. Bioorg. Med. Chem. Lett. 1997, 7, 2687.
27. Bringmann, G.; Wenzel, M.; Kelly, T. R.; Boyd, M. R.; Gulakowski, R. J.; Kaminsky, R. Tetrahedron 1999, 55, 1731.
28. de Koning, C. B.; Michael, J. P.; Otterlo, W. A. L. Tetrahedron Lett. 1999, 40, 3037.
29. Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525.
30. Bringmann, G.; Pokorny, F. In The Alkaloids; Cordell, G., Ed.; Academic Press: New York, 1995; Vol. 46, p 127.
31. Bringmann, G.; Reuscher, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 1672.
32. Bringmann, G.; Jansen, J. R. Synthesis 1991, 825.
33. Bringmann, G.; Saeb, W.; Rübenacker, M. Tetrahedron 1999, 55, 423.
34. For a conceptionally novel approach to the atropisomer-selective construction of korupensamines, see Lipshutz, B. H.; Keith, J. M. Angew. Chem., Int. Ed. 1999, 38, 3530.
35. Hobbs, P. D.; Upender, V.; Dawson, M. I. Synlett 1997, 965.
36. (a) Hoye, T. R.; Chen, M. Tetrahedron Lett. 1996, 37, 3099.
37. (b) Watanabe, T.; Uemura, M. J. Chem. Soc., Chem. Commun. 1998, 871.
38. (c) Rao, A. V. R.; Gurjar, M. K.; Ramana, D. V.; Chheda, A. K. Heterocycles 1996, 43, 1.
39. For an efficient first total synthesis of dioncophylline C, a highly antimalarial naphthylisoquinoline without an oxygen function next to the axis, again by the lactone methodology, with elimination of the "bridgehead oxygen function" after construction of the molecular framework; see ref 20.
40. Bringmann, G.; Ochse, M. Synlett 1998, 1294.
41. Peters, K.; Peters, E.-M.; Ochse, M.; Bringmann, G. Z. Kristallogr. - New Cryst. Struct. 1998, 213, 559.
42. Rao, A. V. R.; Chakraborty, T. K.; Joshi, S. P. Tetrahedron Lett. 1992, 33, 4045.
43. Bringmann, G.; Pabst, T.; Busemann, S.; Peters, K.; Peters, E.-M. Tetrahedron 1998, 64, 1425.
44. 2 and 1.3 equiv of tris(o-tolyl)phosphine, see: Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844.
45. Bringmann, G.; Jansen, J. R.; Rink, H.-P. Angew. Chem., Int. Ed. Engl. 1986, 25, 913.
46. Bringmann, G.; Jansen, J. R. Heterocycles 1989, 28, 137.
47. 2OH of 10b indicated this atropo-diastereomer to be M-configured. This assignment was later on confirmed at the level of the final target molecules, korupensamine A (1a) and B (1b).
48. Separation of 10a and 10b was performed by column chromatography.
49. Bringmann, G.; Göbel, L.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Inorg. Chim. Acta 1994, 222, 255.
50. 49 should lead to a preferred attack of nucleophiles (in particular if these are devoid of additional stereochemical information) from the bottom face, thus leading to the M-atropisomer.
51. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E.; Steward, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
52. Rauhut, G.; Chandrasekhar, J.; Alex, A.; Beck, B.; Sauer, W.; Clark, T. VAMP 6.5 available from Oxford Molecular Ltd., The Medewar Centre, Oxford Science Park, Sandford-on-Thames, Oxford, 0X4 4GA, England.
53. SYBYL: Tripos Associates, 1699 St. Hanley Road, Suite 303, St. Louis, MO, 63144.
54. Bringmann, G.; Vitt, D. J. Org. Chem. 1995, 60, 7674.
55. Bringmann, G.; Breuning, M.; Walter, R.; Wuzik, A.; Peters, K.; Peters, E.-M. Eur. J. Org. Chem. 1999, 3047.
56. Bringmann, G.; Breuning, M. Tetrahedron: Asymmetry 1999, 10, 385.
57. For a review on the oxazaborolidine-borane reagent, mainly for the reduction of carbonyl compounds, see: Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986.
58. 3 system, see refs 54, 38, and 55.
59. Bringmann, G.; Hartung, T. Tetrahedron 1993, 49, 7891.
60. Bringmann, G.; Breuning, M. Tetrahedron: Asymmetry 1998, 9, 667.
61. The use of manganese dioxide did not lead to a quantitative conversion of 14b to 15b.
62. For an easier comparison of the isoquinoline-free naphthalene with the naphthyl parts of the corresponding alkaloids even of different coupling types, a 2-methyl-4,5-dioxy substitution pattern is applied throughout in the numbering of these naphthalenes, regardless of the presence of a biaryl axis; see also ref 27.
63. Bringmann, G.; Ortmann, T.; Feineis, D.; Peters, E.-M.; Peters, K. Synthesis, in press.
64. Bringmann, G.; Schneider, S. Synthesis 1983, 139.
65. (a) Sala, T.; Sargent, M. V. J. Chem. Soc., Perkin Trans. 1 1979, 2593.
66. (b) Greene, T. W. Protective Groups in Organic Synthesis; Wiley: New York, 1981.
67. 60 in the field of naphthylisoquinoline alkaloids, see refs 27, 12, 8, and 20.
68. Bringmann, G.; Wuzik, A.; Breuning, M.; Henschel, P.; Peters, K.; Peters, E.-V. Tetrahedron: Asymmetry 1999, 10, 3025.
69. Owton, W. M.; Gallagher, P. T.; Juan-Montesinos, A. Synth. Commun. 1993, 23, 2119.