Total syntheses of thiocoraline and BE-22179: Establishment of relative and absolute stereochemistry [7]

Journal of the American Chemical Society

Volumn 122, Issue 12, 2000, Pages 2956-2957

  Boger, Dale L ^a   Ichikawa, Satoshi ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; BE 22179; ECHINOMYCIN; THIOCORALINE; TRIOSTIN A; UNCLASSIFIED DRUG;

CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034728553     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0001660     Document Type: Letter

References (38)

1. (a) Romeo, F.; Espliego, F.; Baz, J. P.; de Quesada, T. G.; Gravalos, D.; de la Calle, F.; Fernandez-Puentes, J. L. J. Antibiot. 1997, 50, 734.
2. (b) Perez Baz, J.; Canedo, L. M.; Fernandez-Puentes, J. L. J. Antibiot. 1997, 50, 738.
3. (c) Perez Baz, J.; Millan, F. R.; De Quesada, T. G.; Gravalos, D. G. PCT Int. Appl., WO952773, 1995; Chem. Abstr. 1995, 124, 115561.
4. Okada, H.; Suzuki, H.; Yoshinari, T.; Arakawa, H.; Okura, A.; Suda, H. J. Antibiot. 1994, 47, 129.
5. (a) Shoji, J.; Katagiri, K. J. Antibiot. 1961, 14, 335.
6. (b) Shoji, J.; Tori, K.; Otsuka, H. J. Org. Chem. 1965, 30, 2772.
7. (c) Otsuka, H.; Shoji, J. Tetrahedron 1967, 23, 1535.
8. (d) Otsuka, H.; Shoji, J.; Kawano, K.; Kyogoku, Y. J. Antibiot. 1976, 29, 107.
9. (a) Corbaz, R.; Ettlinger, L.; Graumann, E.; Keller-Schierlein, W.; Kradolfer, F.; Neipp, L.; Prelog, V.; Reusser, P.; Zahner, H. Helv. Chim. Acta 1957, 40, 199.
10. (b) Keller-Schierlein, W.; Prelog, V. Helv. Chim. Acta 1957, 40, 205.
11. (c) Keller-Schierlein, W.; Mihailovic, M. Lj.; Prelog, V. Helv. Chim. Acta 1959, 42, 305.
12. (d) Martin, D. G.; Mizsak, S. A.; Biles, C.; Stewart, J. C.; Baczynskyj, L.; Meulman, P. A. J. Antibiot. 1975, 28, 332.
13. (e) Dell, A.; Williams, D. H.; Morris, H. R.; Smith, G. A.; Feeney, J.; Roberts, G. C. K. J. Am. Chem. Soc. 1975, 97, 2497.
14. (a) Waring, M. J.; Wakelin, L. P. G. Nature 1974, 252, 653.
15. (b) Wang, A. H.-J.; Ughetto, G.; Quigley, G.; Hakoshima, T.; van der Marel, G. A.; van Boom, J. H.; Rich, A. Science 1984, 225, 1115.
16. (c) Quigley, G. J.; Ughetto, G.; van der Marel, G. A.; van Boom, J. H.; Wang, A. H.-J.; Rich, A. Science 1994, 232, 1255.
17. Yoshinari, T.; Okada, H.; Yamada, A.; Uemura, D.; Oka, H.; Suda, H.; Okura, A. Jpn. J. Cancer Res. 1994, 85, 550.
18. (a) Erba, E.; Bergamaschi, D.; Ronzoni, S.; Taverna, S.; Bonfanti, M.; Calapano, C. V.; Faircloth, G.; Jimeno, J.; D'Incalci, M. Br. J. Cancer 1999, 80, 971.
19. (b) Yoshinari, T.; Okada, H.; Yamada, A.; Uemura, D.; Oka, H.; Okura, A. Jpn. J. Cancer Res. 1994, 85, 550.
20. Isolation: Matson, J. A.; Bush, J. A. J. Antibiot. 1989, 42, 1763. Total synthesis: Boger, D. L.; Chen, J.-H. J. Am. Chem. Soc. 1993, 115, 11624. Boger, D. L.; Chen, J.-H.; Saionz, K. W. J. Am. Chem. Soc. 1996, 118, 1629.
21. Isolation: Matson, J. A.; Bush, J. A. J. Antibiot. 1989, 42, 1763. Total synthesis: Boger, D. L.; Chen, J.-H. J. Am. Chem. Soc. 1993, 115, 11624. Boger, D. L.; Chen, J.-H.; Saionz, K. W. J. Am. Chem. Soc. 1996, 118, 1629.
22. Isolation: Matson, J. A.; Bush, J. A. J. Antibiot. 1989, 42, 1763. Total synthesis: Boger, D. L.; Chen, J.-H. J. Am. Chem. Soc. 1993, 115, 11624. Boger, D. L.; Chen, J.-H.; Saionz, K. W. J. Am. Chem. Soc. 1996, 118, 1629.
23. Boger, D. L.; Chen, J.-H.; Saionz, K. W.; Jin, Q. Bioorg. Med. Chem. 1998, 6, 85.
24. Isolation: Konishi, M.; Ohkuma, H.; Sakai, F.; Tsuno, T.; Koshiyama, H.; Naito, T.; Kawaguchi, H. J. Antibiot. 1981, 34, 148. Structure and stereochemistry: Arnold, E.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 1243. Total synthesis (luzopeptins A-C): Boger, D. L.; Ledeboer, M. W.; Kume. M. J. Am. Chem. Soc. 1999, 121, 1098. Boger, D. L.; Ledeboer, M. W.; Kume, M.; Searcey, M.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 11375.
25. Isolation: Konishi, M.; Ohkuma, H.; Sakai, F.; Tsuno, T.; Koshiyama, H.; Naito, T.; Kawaguchi, H. J. Antibiot. 1981, 34, 148. Structure and stereochemistry: Arnold, E.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 1243. Total synthesis (luzopeptins A-C): Boger, D. L.; Ledeboer, M. W.; Kume. M. J. Am. Chem. Soc. 1999, 121, 1098. Boger, D. L.; Ledeboer, M. W.; Kume, M.; Searcey, M.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 11375.
26. Isolation: Konishi, M.; Ohkuma, H.; Sakai, F.; Tsuno, T.; Koshiyama, H.; Naito, T.; Kawaguchi, H. J. Antibiot. 1981, 34, 148. Structure and stereochemistry: Arnold, E.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 1243. Total synthesis (luzopeptins A-C): Boger, D. L.; Ledeboer, M. W.; Kume. M. J. Am. Chem. Soc. 1999, 121, 1098. Boger, D. L.; Ledeboer, M. W.; Kume, M.; Searcey, M.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 11375.
27. Isolation: Konishi, M.; Ohkuma, H.; Sakai, F.; Tsuno, T.; Koshiyama, H.; Naito, T.; Kawaguchi, H. J. Antibiot. 1981, 34, 148. Structure and stereochemistry: Arnold, E.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 1243. Total synthesis (luzopeptins A-C): Boger, D. L.; Ledeboer, M. W.; Kume. M. J. Am. Chem. Soc. 1999, 121, 1098. Boger, D. L.; Ledeboer, M. W.; Kume, M.; Searcey, M.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 11375.
28. Isolation: Lingham, R. B.; Hsu, A. H. M.; O'Brien, J. A.; Sigmund, J. M.; Sanchez, M.; Gagliardi, M. M.; Heimbuch, B. K.; Genilloud, O.; Martin, I.; Diez, M. T.; Hirsch, C. F.; Zink, D. L.; Liesch, J. M.; Koch, G. E.; Garter, S. E.; Garrity, G. M.; Tsou, N. N.; Salituro, G. M. J. Antibiot. 1996, 49, 253. Total synthesis: Boger, D. L.; Ledeboer, M. W.; Kume, M.; Jin, Q. Angew. Chem., Int. Ed. 1999, 38, 2424.
29. Isolation: Lingham, R. B.; Hsu, A. H. M.; O'Brien, J. A.; Sigmund, J. M.; Sanchez, M.; Gagliardi, M. M.; Heimbuch, B. K.; Genilloud, O.; Martin, I.; Diez, M. T.; Hirsch, C. F.; Zink, D. L.; Liesch, J. M.; Koch, G. E.; Garter, S. E.; Garrity, G. M.; Tsou, N. N.; Salituro, G. M. J. Antibiot. 1996, 49, 253. Total synthesis: Boger, D. L.; Ledeboer, M. W.; Kume, M.; Jin, Q. Angew. Chem., Int. Ed. 1999, 38, 2424.
30. Blondeau, P.; Berse, C.; Gravel, D. Can. J Chem. 1967, 45, 49.
31. DCC = dicyclohexylcarbodiimide; EDCI = 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOBt = 1-hydroxybenzotriazole; HOAt = 1-hydroxy-7-azabenzotriazole.
32. DPPA = diphenyl phosphorazidate; DEPC = diethyl phosphorocyanidate. (a) Yamada, S.; Yokoyama, Y.; Shioiri, T. J. Org. Chem. 1974, 39, 3302. (b) Yokoyama, Y.; Shioiri, T.; Yamada, S. Chem. Pharm. Bull. 1977, 25, 2423.
33. DPPA = diphenyl phosphorazidate; DEPC = diethyl phosphorocyanidate. (a) Yamada, S.; Yokoyama, Y.; Shioiri, T. J. Org. Chem. 1974, 39, 3302. (b) Yokoyama, Y.; Shioiri, T.; Yamada, S. Chem. Pharm. Bull. 1977, 25, 2423.
34. Kamber, B.; Hartmann, A.; Eisler, K.; Riniker, B.; Rink, H.; Sieber, P.; Rittel, W. Helv. Chim. Acta 1980, 63, 899.
35. Kiso, Y.; Ukawa, K.; Akita, T. J. Chem. Soc. Chem. Commun. 1980, 101.
36. 2O 3/1/1, 25°C, 2 h (71%).
37. Boger, D. L.; Chen, J.-H. J. Org. Chem. 1995, 60, 7369.
38. Preliminary efforts enlisting Fmoc and basic deprotection conditions vs Cbz protecting groups on 23 failed to provide 24 or 1. In addition, effort to first form the symmetrical disulfide of 16 followed by simultaneous formation of both secondary amides of the macrocycle led to a complex mixture of products.