An epiisopicropodophyllin aza analogue via palladium-catalyzed pseudo-domino cyclization

Journal of Organic Chemistry

Volumn 67, Issue 26, 2002, Pages 9456-9459

  Poli, Giovanni ^a   Giambastiani, Giuliano ^b  

^a CNRS   (France)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; PALLADIUM;

SINGLE SYNTHETIC OPERATIONS;

ORGANIC COMPOUNDS;

EPIISOPICROPODOPHYLLIN; PALLADIUM; PODOPHYLLIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; SYNTHESIS;

AZA COMPOUNDS; CATALYSIS; CYCLIZATION; ETOPOSIDE; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PALLADIUM; PODOPHYLLOTOXIN; STEREOISOMERISM;

EID: 0037184777     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026068+     Document Type: Article

References (68)

1. (a) Damayanthi, Y.; Lown, J. W. Curr. Med. Chem. 1998, 5, 205-252.
2. (b) Zhang, Y.; Lee, K.-H. Chin. Pharm. J. 1994, 46, 319-369.
3. (c) Ramos, A. C.; Pelaéz-Lamamié de Clairac, R.; Medarde, M. Heterocycles 1999, 51, 1443-1470.
4. (d) Ward, R. S. Chem. Soc. Rev. 1982, 75-125.
5. (e) Ward, R. S. Synthesis 1992, 719-730.
6. (a) Katritzky, A. R.; Cobo-Domingo, J.; Yang, B.; Steel, P. J. Tetrahedron: Asymmetry 1999, 10, 255-263.
7. (b) Hitotsuyanagi, Y.; Yamagami, K.; Fujii, A.; Naka, Y.; Ito, Y.; Tahara, T. Biorg. Med. Chem. Lett. 1995, 5, 1039-1042.
8. (c) Hitotsuyanagi, Y.; Kobayashi, M.; Takeya, K.; Itokawa, H. J. Chem. Soc., Perkin Trans. 1 1995, 1387-1390.
9. (d) Hitotsuyanagi, Y.; Naka, Y.; Yamagami, K.; Fujii, A.; Tahara, T. Chem. Commun. 1995, 49-50.
10. (e) Hitotsuyanagi, Y.; Ichihara, Y.; Takeya, K. Itokawa, H. Tetrahedron Lett. 1994, 35, 9401-9402.
11. (f) Tomioka, K.; Kubota, Y.; Koga, K. Tetrahedron 1993, 49, 1891-1900.
12. (g) Lienard, P.; Quirion, J.-C.; Husson, H.-P. Tetrahedron 1993, 49, 3995-4006.
13. (h) Tomioka, K.; Kubota, Y.; Koga, K. Chem. Commun. 1989, 1622-1624.
14. (i) Van der Eycken, J.; Bosmans, J.-P.; Van Haver, D.; Vandewalle, M. Tetrahedron Lett. 1989, 30, 3873-3876.
15. (j) Bosmans, J.-P.; Van der Eycken, J.; Vandewalle, M.; Hulkenberg, A.; Van Hes, R.; Veerman, W. Tetrahedron Lett. 1989, 30, 3877-3880.
16. (k) Pearce, H. L.; Bach, N. J. Cramer, T. L. Tetrahedron Lett. 1989, 30, 907-910.
17. (l) Tomioka, K.; Kubota, Y.; Koga, K. Tetrahedron Lett. 1989, 30, 2953-2954.
18. Clark, P. I.; Slevin, M. L. Clin. Pharmacokinet. 1987, 12, 223-252.
19. Gensler, W. J.; Murthy, C. D.; Trammel, M. H. J. Med. Chem. 1977, 20, 635-644.
20. (a) Jardine, I.; Strife, R. J.; Kozlowski, J. J. Med. Chem. 1982, 25, 1077-1081.
21. (b) Zhou, X. M.; Lee, K. J.-H.; Cheng, J.; Wu, S.-S.; ChenH.-X.; Guo, X.; Cheng, Y.-C.; Lee, K.-H. J. Med. Chem. 1994, 37, 287-292.
22. (c) Subrahmanyam, D.; Renuka, B.; Kumar, G. S.; Vandana, V.; Deevi, D. S. Bioorg. Med. Chem. Lett. 1999, 9, 2131-2134.
23. (a) Roulland, E.; Bertounesque, E.; Huel, C.; Monneret, C. Tetrahedron Lett, 2000, 41, 6769-6773.
24. (b) Jurd, L. J. Heterocycl. Chem. 1996, 33, 1227-1232.
25. (a) Kadow, J. F.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1989, 30, 3299-3302.
26. (b) Kadow, J. F.; Vyas, D. M. Eur. Pat. Appl. EP 329, 108, 1990; Chem. Abstr. 1990, 112, 56571k.
27. (b) Kadow, J. F.; Vyas, D. M. Eur. Pat. Appl. EP 329, 108, 1990; Chem. Abstr. 1990, 112, 56571k.
28. (a) Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
29. For other related reviews see: (b) Tietze, L. F.; Haunert, F. In Stimulating Concepts in Chemistry; Shibasaki, M., Stoddart, J. F., Vögtle, F., Eds.; Wiley-VCH: Weinheim, 2000; pp 39-64.
30. (c) Tietze, L. F. Chem. Ind. 1995, 453-457.
31. (d) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163.
32. (e) Ho, T. L. Tandem Organic Reactions; Wiley: New York, 1992.
33. (f) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1332-1334.
34. (g) Tietze, L. F. J. Heterocycl. Chem. 1990, 27, 47-69.
35. (h) Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452.
36. (i) Posner, G. H. Chem. Rev. 1986, 86, 831-844.
37. We warmly thank a referee for having provided us with the fundamental concepts enabling articulation of the principles underlying Figure 2.
38. For the sake of straightforwardness we propose the intuitive acronyms TM-DOM and TM-PDOM to designate the transition metal- catalyzed domino and pseudo-domino processes, respectively, TM indicating the generic transition metal involved in the catalysis.
39. Of course, the real active catalysts driving each of the two sequential transformations may differ from one another, although deriving from the same catalytic system.
40. Poli, G.; Giambastiani, G.; Heumann, A. Tetrahedron 2000, 56, 5959-5989.
41. Poli, G.; Giambastiani, G.; Pacini, B. Tetrahedron Lett. 2001, 42, 5179-5182.
42. Tietze, L. F.; Nordmann, G. Eur. J. Org. Chem. 2001, 3247-3253.
43. Jeong, N.; Seo, D.; Shin, J.-Y. J. Am. Chem. Soc. 2000, 122, 10220-10221.
44. For two recently published palladium-catalyzed pure-domino processes involving carbopalladation/allylation see: (a) Shimizu, I.; Lee, Y.; Fujiwara, Y. Synlett 2000, 1285-1286.
45. (b) Flubacher, D.; Helmchen, G. Tetrahedron Lett. 1999, 40, 3867-3868.
46. For a recent total synthesis of (-)-podophyllotoxin see: (a) Berkowitz, D. B.; Choi, S.; Maeng, J.-H. J. Org. Chem. 2000, 65, 847-860.
47. For a recent B-ring modification see: (b) Ramos, A. C.; Peláez, R.; López, J. L.; Caballero, E.; Medarde, M.; san Feliciano, A. Tetrahedron 2001, 57, 3963-3977.
48. For approaches to related structures via palladium chemistry see: (c) Ishibashi, H.; Ito, K.; Hirano, T.; Tabuchi, M.; Ikeda, M. Tetrahedron 1993, 49, 4173-4182.
49. (d) Galland, J.-C.; Dias, S.; Savignac, M.; Genêt, J.-P. Tetrahedron 2001, 57, 5137-5148.
50. (e) Charruault, L.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 4757-4760.
51. Giambastiani, G.; Pacini, B.; Porcelloni, M.; Poli, G. J. Org. Chem. 1998, 63, 804-807.
52. Aoyama, T.; Sonoda, N.; Yamauchi, M.; Toriyama, K.; Anzai, M.; Ando, A.; Shioiri, T. Synlett 1998, 35-36.
53. Conrad, P. C.; Kwiatkowski, P. L.; Fuchs, P. L. J. Org. Chem. 1987, 52, 586-591.
54. Brown, E.; Lésé, A.; Touet, J. Tetrahedron: Asymmetry 1992, 3, 841-844.
55. Bream, J. B.; Schmutz, J. Helv. Chim. Acta 1977, 60, 2872-2880.
56. N2 substitution process. In fact, an analogous transformation using o-bromobenzhydryl bromide instead of 12 gave the desired alkylated product in high yield.
57. Adams, J. T.; Levine, R.; Hauser, C. R. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, pp 405-407.
58. Bisaro, F.; Prestat, G.; Vitale, M.; Poli, G. Synlett 2002, 1823-1826.
59. 1H NMR owing to amide bond effect.
60. 2:dppe:AcOK:13 = 0.1:0.2:1.0.
61. See Supporting Information.
62. The value of the allylic coupling constants in both the diastereoisomers 14 was essentially zero. Previous studies in the laboratory indicated that such a feature is associated to cis junction.
63. (a) Krapcho, A. P. Synthesis 1982, 805-822.
64. (b) Krapcho, A. P. Synthesis 1982, 893-914.
65. Brewer, C. F.; Loike, J. D.; Horwitz, S. B.; Sternlicht, H.; Gensler, W. J. J. Med. Chem. 1979, 22, 215-221.
66. 2.3 = 9.16 Hz.
67. 4 reduction of the minor diastereoisomer 16b gave quantitatively alcohol 17b (structure not shown in the publication) as the only detectable epimer.
68. Forsey, S. P.; Rajapaksa, D.; Taylor, N. J.; Rodrigo, R. J. Org. Chem. 1989, 54, 4280-4290.