Synthesis of the marine sponge cycloheptapeptide stylopeptide 1

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2322-2325

  Pettit, George R ^a   Taylor, Stuart R ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; STYLOPEPTIDE 1; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; TUMOR CELL;

EID: 0029874160     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951986b     Document Type: Article

References (34)

1. Unit 346 in the series "Antineoplastic Agents" and for the preceding report see: Jayson, G. C.; Crowther, D.; Prendiville, J.; McGown, A. T.; Scheid, C.; Stern, P.; Young, R.; Brenchley, P. Chang, J.; Owens, S.; Pettit, G. R. Br. J. Cancer 1995, 72, 461.
2. (a) Pettit, G. R.; Srirangam, J. R.; Herald, D. L.; Erickson, K. L.; Doubek, D. L.; Schmidt, J. M.; Tackett, L. P.; Bakus, G. J. J. Org. Chem. 1992, 57, 7217.
3. (b) Pettit, G. R.; Srirangam, J. K.; Herald, D. L.; Xu, J.-P.; Boyd, M. R.; Cichacz, Z.; Kamano, Y.; Schmidt, J. M.; Erickson, K. L. J. Org. Chem. 1995, 60, 8257.
4. (c) Unpublished results.
5. (a) Pettit, G. R.; Tan, R.; Gao, F.; Williams, M. D.; Doubek, D. L.; Boyd, M. R.; Schmidt, J. M.; Chapuis, J.-C.; Hamel, E.; Bai, R.; Hooper, J. N. A.; Tackett, L. P. J. Org. Chem. 1993, 58, 2538.
6. (b) Pettit, G. R.; Gao, F.; Doubek, D. L.; Boyd, M. R.; Hamel, E.; Bai, R.; Schmidt, J. M.; Tackett, L. P.; Rutzler, K. Gazz. Chim. Ital. 1993, 123, 371.
7. (a) Perich, J. W.; Johns, R. B. Aust. J. Chem. 1990, 43, 1623; Riniker, B.; Flörsheimer, A.; Fretz, H ; Sieber, P.; Kamber, B. Tetrahedron 1993, 49, 9307.
8. (a) Perich, J. W.; Johns, R. B. Aust. J. Chem. 1990, 43, 1623; Riniker, B.; Flörsheimer, A.; Fretz, H ; Sieber, P.; Kamber, B. Tetrahedron 1993, 49, 9307.
9. (b) For an exception see Fischer, P. M.; Solbakken, M.; Undheim, K. Tetrahedron, 1994, 50, 2277. (c) Tung, R. D.; Dhaon, M. K.; Rich, D. H. J. Org. Chem. 1986, 51, 3350. (d) Høeg-Jensen, T.; Jakobsen, M. H.; Holm, A. Tetrahedron Lett. 1991, 32, 6387. (e) Paulsen, H.; Adermann, K. Liebigs Ann. Chem., 1989, 751 and 771.
10. (b) For an exception see Fischer, P. M.; Solbakken, M.; Undheim, K. Tetrahedron, 1994, 50, 2277. (c) Tung, R. D.; Dhaon, M. K.; Rich, D. H. J. Org. Chem. 1986, 51, 3350. (d) Høeg-Jensen, T.; Jakobsen, M. H.; Holm, A. Tetrahedron Lett. 1991, 32, 6387. (e) Paulsen, H.; Adermann, K. Liebigs Ann. Chem., 1989, 751 and 771.
11. (b) For an exception see Fischer, P. M.; Solbakken, M.; Undheim, K. Tetrahedron, 1994, 50, 2277. (c) Tung, R. D.; Dhaon, M. K.; Rich, D. H. J. Org. Chem. 1986, 51, 3350. (d) Høeg-Jensen, T.; Jakobsen, M. H.; Holm, A. Tetrahedron Lett. 1991, 32, 6387. (e) Paulsen, H.; Adermann, K. Liebigs Ann. Chem., 1989, 751 and 771.
12. (b) For an exception see Fischer, P. M.; Solbakken, M.; Undheim, K. Tetrahedron, 1994, 50, 2277. (c) Tung, R. D.; Dhaon, M. K.; Rich, D. H. J. Org. Chem. 1986, 51, 3350. (d) Høeg-Jensen, T.; Jakobsen, M. H.; Holm, A. Tetrahedron Lett. 1991, 32, 6387. (e) Paulsen, H.; Adermann, K. Liebigs Ann. Chem., 1989, 751 and 771.
13. Pettit, G. R.; Holman, J. W.; Boland, G. M. J. Chem. Soc., Perkin Trans. 1, submitted.
14. Adamson, J. G.; Blaskovich, M. A.; Groenevelt, H.; Lajoie, G. A. J. Org. Chem. 1991, 56, 3447. We obtained lower yields with this procedure using excess p-toluenesulfonic acid compared to a catalytic amount of sulfuric acid. Costopanagiotis, A. A.; Preston, J.; Weinstein, B. J. Org. Chem. 1966, 31, 3398. Roeske, R. J. Org. Chem. 1963, 28, 1251. Anderson, G. W.; Callahan, F. M. J. Am. Chem. Soc. 1960, 82, 3359.
15. Adamson, J. G.; Blaskovich, M. A.; Groenevelt, H.; Lajoie, G. A. J. Org. Chem. 1991, 56, 3447. We obtained lower yields with this procedure using excess p-toluenesulfonic acid compared to a catalytic amount of sulfuric acid. Costopanagiotis, A. A.; Preston, J.; Weinstein, B. J. Org. Chem. 1966, 31, 3398. Roeske, R. J. Org. Chem. 1963, 28, 1251. Anderson, G. W.; Callahan, F. M. J. Am. Chem. Soc. 1960, 82, 3359.
16. Adamson, J. G.; Blaskovich, M. A.; Groenevelt, H.; Lajoie, G. A. J. Org. Chem. 1991, 56, 3447. We obtained lower yields with this procedure using excess p-toluenesulfonic acid compared to a catalytic amount of sulfuric acid. Costopanagiotis, A. A.; Preston, J.; Weinstein, B. J. Org. Chem. 1966, 31, 3398. Roeske, R. J. Org. Chem. 1963, 28, 1251. Anderson, G. W.; Callahan, F. M. J. Am. Chem. Soc. 1960, 82, 3359.
17. Adamson, J. G.; Blaskovich, M. A.; Groenevelt, H.; Lajoie, G. A. J. Org. Chem. 1991, 56, 3447. We obtained lower yields with this procedure using excess p-toluenesulfonic acid compared to a catalytic amount of sulfuric acid. Costopanagiotis, A. A.; Preston, J.; Weinstein, B. J. Org. Chem. 1966, 31, 3398. Roeske, R. J. Org. Chem. 1963, 28, 1251. Anderson, G. W.; Callahan, F. M. J. Am. Chem. Soc. 1960, 82, 3359.
18. (a) For a review see: Fields, G. B.; Noble, R. L. Int. J. Pept. Protein Res. 1990, 35, 161. (b) Chang, C.; Waki, M.; Ahmad, M.; Meienhofer, J.; Lundell, E. O.; Haug, J. D. Int. J. Pept. Protein Res. 1980, 15, 59. (c) Bodanszky, M.; Deshmane, S. S.; Martinez, J. J Org. Chem. 1979, 44, 1622.
19. (a) For a review see: Fields, G. B.; Noble, R. L. Int. J. Pept. Protein Res. 1990, 35, 161. (b) Chang, C.; Waki, M.; Ahmad, M.; Meienhofer, J.; Lundell, E. O.; Haug, J. D. Int. J. Pept. Protein Res. 1980, 15, 59. (c) Bodanszky, M.; Deshmane, S. S.; Martinez, J. J Org. Chem. 1979, 44, 1622.
20. (a) For a review see: Fields, G. B.; Noble, R. L. Int. J. Pept. Protein Res. 1990, 35, 161. (b) Chang, C.; Waki, M.; Ahmad, M.; Meienhofer, J.; Lundell, E. O.; Haug, J. D. Int. J. Pept. Protein Res. 1980, 15, 59. (c) Bodanszky, M.; Deshmane, S. S.; Martinez, J. J Org. Chem. 1979, 44, 1622.
21. Hamada, Y.; Rishi, S.; Shioiri, T.; Yamada, S.-I. Chem. Pharm. Bull. 1977, 25, 224. DEPC is also called diethylphosphoryl cyanide or diethyl cyanophosphonate.
22. Benoiton, N. L. Int. J. Pept. Protein Res. 1994, 44, 399.
23. Haver, A. C.; Smith, D. D. Tetrahedron Lett. 1993, 34, 2239. Miyazawa, T.; Otomatsu, T.; Yamada, T.; Kuwata, S. Int. J. Pept. Protein Res. 1992, 39, 229. Benoiton, N. L.; Kuroda, K. Int. J. Pept. Protein Res. 1981, 17, 197.
24. Haver, A. C.; Smith, D. D. Tetrahedron Lett. 1993, 34, 2239. Miyazawa, T.; Otomatsu, T.; Yamada, T.; Kuwata, S. Int. J. Pept. Protein Res. 1992, 39, 229. Benoiton, N. L.; Kuroda, K. Int. J. Pept. Protein Res. 1981, 17, 197.
25. Haver, A. C.; Smith, D. D. Tetrahedron Lett. 1993, 34, 2239. Miyazawa, T.; Otomatsu, T.; Yamada, T.; Kuwata, S. Int. J. Pept. Protein Res. 1992, 39, 229. Benoiton, N. L.; Kuroda, K. Int. J. Pept. Protein Res. 1981, 17, 197.
26. Schmidt, U.; Langner, J. J. Chem. Soc., Chem. Commun. 1994, 2381.
27. (a) Zimmer, S.; Hoffmann, E.; Jung, G.; Kessler, H. Liebigs Ann. Chem. 1993, 497.
28. (b) Trzeciak, A.; Bannwarth, W. Tetrahedron Lett. 1992, 33, 4557.
29. Ehrlich, A.; Rothemund, S.; Brudel, M.; Beyermann, M.; Carpino, L. A.; Bienert, M. Tetrahedron Lett. 1993, 34, 4781.
30. Suggested by Prof. R. B. Bates, University of Arizona. Also designated N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride.
31. Burke, T. R., Jr.; Knight, M.; Chandrasekhar, B.; Ferretti, J. A. Tetrahedron Lett. 1989, 30, 519. Fischer, P. M.; Retson, K. V.; Tyler, M. I.; Howden, M. E. H. Int. J. Pept. Protein Res. 1991, 38, 491. Barbato, G.; D'Auria, G.; Paolillo, L.; Zanotti, G. Int. J. Pept. Protein Res. 1991, 37, 388.
32. Burke, T. R., Jr.; Knight, M.; Chandrasekhar, B.; Ferretti, J. A. Tetrahedron Lett. 1989, 30, 519. Fischer, P. M.; Retson, K. V.; Tyler, M. I.; Howden, M. E. H. Int. J. Pept. Protein Res. 1991, 38, 491. Barbato, G.; D'Auria, G.; Paolillo, L.; Zanotti, G. Int. J. Pept. Protein Res. 1991, 37, 388.
33. Burke, T. R., Jr.; Knight, M.; Chandrasekhar, B.; Ferretti, J. A. Tetrahedron Lett. 1989, 30, 519. Fischer, P. M.; Retson, K. V.; Tyler, M. I.; Howden, M. E. H. Int. J. Pept. Protein Res. 1991, 38, 491. Barbato, G.; D'Auria, G.; Paolillo, L.; Zanotti, G. Int. J. Pept. Protein Res. 1991, 37, 388.
34. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.