Conversion of Marcfortine A to Paraherquamides via a. Novel Platinum-Oxygen-Mediated Ring Contracting Reaction

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7836-7840

  Lee, Byung H ^a   Clothier, Michael F ^a   Pickering, Dacia A ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHELMINTIC AGENT; MARCFORTINE A; MARCFORTINE A DERIVATIVE; PARAHERQUAMIDE; PARAHERQUAMIDE A; PARAHERQUAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

EID: 0030859892     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971227o     Document Type: Article

References (33)

1. Lynn, R. C. Georgis' Parasitology for Veterinarians; W. B. Saunders Co.: Philadelphia, 1995; p 247.
2. Prichard, R. Vet. Parasitol. 1994, 54, 259.
3. (a) Blizzard, T. A.; Mrozik, H.; Fisher, M. H.; Schaeffer, S. M. J. Org. Chem. 1990, 55, 2256.
4. (b) Blizzard, T. A.; Margiatto, G.; Mrozik, H.; Schaeffer, S. M.; Fisher, M. H. Tetrahedron Lett. 1991, 32, 2441.
5. (c) Shoop, W. L.; Egerton, J. R.; Eary, C. H.; Suhayda, D. J. Parasitology 1990, 76, 349.
6. (d) Ostlind, D. A.; Mickle, W. G.; Ewanciw, D. V.; Andriuli, F. J.; Campbell, W. C.; Hernandez, S.; Mochale, S.; Munguira, E. Res. Vet. Sci. 1990, 48, 260.
7. (e) Blizzard, T. A.; Marino, G.; Sinclair, P. J.; Mrozik, H. European Pat. Appl. EP 0 354 615 A1, 1990; Chem. Abstr. 1990, 113, P131885s.
8. (e) Blizzard, T. A.; Marino, G.; Sinclair, P. J.; Mrozik, H. European Pat. Appl. EP 0 354 615 A1, 1990; Chem. Abstr. 1990, 113, P131885s.
9. (f) Schaeffer, J. M.; Blizzard, T. A.; Ondeyka, J.; Goegelman, R.; Sinclair, P. J.; Mrozik, H. Biochem. Pharmacol. 1992, 43, 679.
10. (g) Mrozik, H. U.S. Pat. Appl. US 4,866,060, 1989; Chem. Abstr. 1990, 112, P48776r.
11. (g) Mrozik, H. U.S. Pat. Appl. US 4,866,060, 1989; Chem. Abstr. 1990, 112, P48776r.
12. (h) Blizzard, T. A.; Mrozik, H. U.S. Pat. Appl. US 4,923,867, 1990; Chem. Abstr. 1991,114, P62467p.
13. (h) Blizzard, T. A.; Mrozik, H. U.S. Pat. Appl. US 4,923,867, 1990; Chem. Abstr. 1991,114, P62467p.
14. (a) Yamazaki, M.; Okuyama, E.; Kobayashi, M.; Inoue, H. Tetrahedron Lett. 1981,22,135.
15. (b) Ondeyka, J. G.; Goegelman, R. T.; Schaeffer, J. M.; Kelemen, L.; Zitano, L. J. Antibiot. 1990, 43, 1375.
16. Liesch, J.; Wichmann, C. J. Antibiot. 1990, 43, 1380.
17. Blanchflower, S. E.; Banks, R. M.; Everett, J. R.; Manger, B. R.; Reading, C. J. Antibiot. 1991, 44, 492.
18. (e) Blanchflower, S. E.; Banks, R. M.; Everett, J. R.; Reading, C. J. Antibiot. 1993, 46, 1355.
19. (f) Perry, D. A., Pet. Int. Appl. WO 92/00300, 1992; Chem. Abstr. 1992, 117, P88729n.
20. (f) Perry, D. A., Pet. Int. Appl. WO 92/00300, 1992; Chem. Abstr. 1992, 117, P88729n.
21. (a) Cushing, T. D.; Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 1996, 118, 557.
22. (b) Williams, R. M.; Jianhua, C. Tetrahedron Lett. 1996, 37, 5441.
23. Lee, B. H.; Clothier, M. F. J. Org. Chem. 1997, 62, 1795.
24. (a) Lee, B. H.; Han, F. Tetrahedron Lett. 1994, 35, 1135.
25. (b) Polonsky, J; Merrien, M. A.; Prange, T.; Pascard, C.; Moreau, S. J. Chem. Soc., Chem. Commun. 1980, 13, 601.
26. Sneeden, R. P. A.; Turner, R. B. J. Am. Chem. Soc. 1955, 77, 190.
27. Muxfeldt, H.; Buhr, G.; Bangert, R. Angew. Chem., Int. Ed. Engl. 1962, 1, 157.
28. Sakamaki, H.; Take, M.; Akihisa, T.; Matsumoto, T.; Ichinohe, Y. Bull. Chem. Soc. Jpn. 1988, 61, 3023.
29. Wasserman, H. H.; Ives, J. L. Tetrahedron 1981, 37, 1825.
30. (a) Bhatt, M. V. Tetrahedron 1964, 20, 803.
31. (b) Aoyage, P.; Moriyama, Y.; Tsuyuki, T.; Takahashi, T. Bull. Chem. Soc. Jpn. 1973, 46, 569.
32. Lee, B. H.; Clothier, M. F. J. Org. Chem. 1997, 62, 1863.
33. Solomon, M.; Jamisom, C. L.; McCormick, M.; Maryanoff, C. A. J. Am. Chem. Soc. 1988, 110, 3702.