Flexible synthesis of metacycloprodigiosin and functional derivatives thereof

Journal of Organic Chemistry

Volumn 64, Issue 22, 1999, Pages 8281-8286

  Fürstner, Alois ^a   Krause, Helga ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRONE DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; METACYCLOPRODIGIOSIN; METACYCLOPRODIGIOSIN DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; HYDROGENATION; IMMUNOSUPPRESSIVE TREATMENT; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

EID: 0042880263     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991022a     Document Type: Article

References (55)

1. (a) Lin, J. Immunol. Today 1993, 14, 290.
2. (b) Nakamura, A.; Nagai, K.; Ando, K.; Tamura, G. J. Antibiot. 1986, 39, 1155.
3. (c) Tsuji, R. F.; Yamamoto, M.; Nakamura, A.; Kataoka, T.; Magae, J.; Nagai, K.; Yamasaki, M. J. Antibiot. 1990, 43, 1293.
4. (d) Kataoka, T.; Magae, J.; Nariuchi, H.; Yamasaki, M.; Nagai, K. J. Antibiot. 1992, 45, 1303.
5. (e) Tsuji, R. F.; Magae, J.; Yamashita, M.; Nagai, K.; Yamasaki, M. J. Antibiot. 1992, 45, 1295.
6. (f) Kataoka, T.; Magae, J.; Kasamo, K.; Yamanishi, H.; Endo, A.; Yamasaki, M.; Nagai, K. J. Antibiot. 1992, 45,1618.
7. (g) Kataoka, T.; Muroi, M.; Ohkuma, S.; Waritani, T.; Magae, J.; Takatsuki, A.; Kondo, S.; Yamasaki, M.; Nagai, K. FEBS Lett. 1996, 359, 53.
8. (h) Lee, M.-H.; Yamashita, M.; Tsuji, R. F.; Yamasaki, M.; Kataoka, T.; Magae, J.; Nagai, K. J. Antibiot. 1998, 51, 92.
9. (i) Han, S. B.; Kim, H. M.; Kim, Y. H.; Lee, C. W.; Jang, E.-S.; Son, K. H.; Kim, S. U.; Kim, Y. K. Int. J. Immunopharmacol. 1998, 20, 1.
10. (j) Sato, T.; Konno, H.; Tanaka, Y.; Kataoka, T.; Nagai, K.; Wasserman, H. H.; Ohkuma, S. J. Biol. Chem. 1998, 273, 21455.
11. (k) Nakamura, A.; Magae, J.; Tsuji, R. F., Yamasaki, M.; Nagai, K. Transplantation 1989, 47, 1013.
12. Songia, S.; Mortellaro, A.; Taverna, S.; Fornasiero, C.; Schreiber, E. A.; Erba, E.; Colotta, F.; Mantovani, A.; Isetta, A.-M.; Golay, J. J. Immunol. 1997, 158, 3987.
13. Compound 1 is available e. g. by fermentation of Streptomyces hiroshimensis, cf. Harashima, K.; Tsuchida, N.; Tanaka, T.; Nagatsu, J. Agric. Biol. Chem. 1967, 31, 481.
14. 1 phase, mostly downstream from the interaction of IL-2 with its receptor, cf. ref 2.
15. (a) Magae, J.; Miller, M.; Nagai, K.; Shearer, G. M. J. Antibiot. 1996, 49, 86.
16. (b) Abe, F.; Morimoto, M.; Shibuya, K.; Yamazaki, M.; Nishigori, T.; Saito, S.; Shimada, N. Jpn. Kokai Tokkyo Koho JP 02,250,828 [90,250,828], Oct 8, 1990. Chem. Abstr. 1990, 114: 108967g.
17. Fürstner, A.; Grabowski, J.; Lehmann, C. W. J. Org. Chem. 1999, 64, 8275.
18. Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
19. For previous synthetic studies on metacycloprodigiosin, see: (a) Wasserman, H. H.; Rodgers, G. C.; Keith, D. D. J. Am. Chem. Soc. 1969, 91, 1263.
20. (b) Wasserman, H. H.; Keith, D. D.; Nadelson, J. J. Am. Chem. Soc. 1969, 97, 1264.
21. (c) Wasserman, H. H.; Keith, D. D.; Rodgers, G. C. Tetrahedron 1976, 32, 1855.
22. (d) Wasserman, H. H.; Gosselink, E.; Keith, D. D.; Nadelson, J.; Sykes, R. J. Tetrahedron 1976, 32, 1863.
23. (e) Wasserman, H. H.; Keith, D. D.; Nadelson, J. Tetrahedron 1976, 32, 1867.
24. For previous syntheses of other prodigiosins derivatives, see inter alia: (a) Hearn, W. R.; Elson, M. K.; Williams, R. H.; Medina-Castro, J. J. Org. Chem. 1970, 35, 142.
25. (b) Wasserman, H. H.; Lombardo, L. J. Tetrahedron Lett. 1989, 1725.
26. (c) Rapoport, H.; Holden, K. G. J. Am. Chem. Soc. 1962, 84, 635.
27. (d) Boger, D. L.; Patel, M. Tetrahedron Lett. 1987, 28, 2499.
28. (e) Boger, D. L.; Patel, M. J. Org. Chem. 1988, 53, 1405.
29. For preparation and the biological evaluation of prodigiosin analogues, see the following for leading references: (a) Brown, D.; Griffiths, D.; Rider, M. E.; Smith, R. C. J. Chem. Soc., Perkin Trans. 1 1986, 455.
30. (b) Blake, A. J.; Hunter, G. A.; McNab, H. J. Chem. Soc., Chem. Comun. 1990, 734.
31. (c) Berner, H.; Schulz, G.; Reinshagen, H. Monatsh. Chem. 1977, 108, 233.
32. (d) Berner, H.; Schulz, G.; Reinshagen, H. Monatsh. Chem. 1978, 109, 137.
33. (e) Berner, H.; Schulz, G.; Reinshagen, H. Monatsh. Chem. 1977, 108, 285.
34. (f) Berner, H.; Schulz, G.; Fischer, G.; Reinshagen, H. Monatsh. Chem. 1978, 109, 557.
35. (g) Castro, A. J.; Gale, G. R.; Means, G. E.; Tertzakian, G. J. Med. Chem. 1967, 10, 29.
36. (h) D'Auria, M.; De Luca, E.; Mauriello, G.; Racioppi, R. Synth. Commun. 1999, 29, 35.
37. (a) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1997, 119, 2944.
38. (b) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817.
39. (c) Fürstner, A.; Gastner, T.; Weintritt, H. J. Org. Chem. 1999, 64, 2361.
40. A large scale preparation is described in the Supporting Information.
41. For an application of this building block to a furan synthesis, see: Fürstner, A.; Gastner, T. Synlett 1999, 29.
42. (a) tert-BuLi was recommended as the deprotonating agent of choice, cf.: LaRochelle, R. W.; Trost, B. M.; Krepski, L. J. Org. Chem. 1971, 36, 1126.
43. (b) Review: Trost, B. M.; Melvin, L. S. Sulfur Ylides; Organic Chemistry Series; Academic Press: New York, 1975; Vol. 31.
44. For pertinent reviews on Pd(0)-catalyzed reactions of vinyl epoxides, see: (a) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1995.
45. (b) Trost, B. M. Angew. Chem. 1989, 101, 1199.
46. The same is true for compounds 9-13 in Scheme 2.
47. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
48. (b) Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
49. Full information on the X-ray structure of compound 14 is given in the Supporting Information. The complete set of data has been deposited at the Cambridge Crystallographic Data Center, Cambridge, UK, under the deposition number CCDC 127650.
50. For details, see the Supporting Information.
51. For a timely and comprehensive review on the Paal-Knorr and related pyrrole syntheses, see: Gossauer, A. In Houben-Weyl, Methoden der Organischen Chemie; Kreher, R. R., Ed.; Thieme: Stuttgart, 1994; Vol. E 6a, Part 1, pp 556-798.
52. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
53. Krapcho, P. A. Synthesis 1982, 893.
54. Crabtree, R. H.; Felkin, H.; Fellebeen-Khan, T.; Morris, G. E. J. Organomet. Chem. 1979, 168, 183.
55. For a review on the Peterson olefination, see: Ager, D. J. Org. React. 1990, 38, 1.