Enantioselective total synthesis of antifungal agent Sch 38516

Journal of the American Chemical Society

Volumn 118, Issue 44, 1996, Pages 10926-10927

  Xu, Zhongmin ^a   Johannes, Charles W ^a   Salman, Sarri S ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; SCH 38516; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029846989     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9626603     Document Type: Article

References (39)

1. (a) Hegde, V. R.; Patel, M. G.; Gullo, V. P.; Ganguly, A. K.; Sarre, O.; Puar, M. S.; McPhail, A. T. J. Am. Chem. Soc. 1990, 112, 6403-6405.
2. (b) Hegde, V. R.; Patel, M.; Horan, A.; Gullo, V.; Marquez, J.; Gunnarsson, I.; Gentile, F.; Loebenberg, D.; King, A. J. Antibiot. 1992, 45, 624-632.
3. (a) Naruse, N.; Tenmyo, O.; Kawano, K.; Tomita, K.; Ohgusa, N.; Miyaki, T.; Konishi, M.; Oki, T. J. Antibiot. 1991, 44, 733-740.
4. (b) Naruse, N.; Tsuno, T.; Sawada, Y.; Konishi, M.; Oki, T. J. Antibiot. 1991, 44, 741-755.
5. (c) Naruse, N.; Konishi, M.; Oki, T. J. Antibiot. 1991, 44, 756-761.
6. (d) Komita, K.; Oda, N.; Hoshino, Y.; Ohkusa, N.; Chikazawa, H. J. Antibiot. 1991, 44, 940-948.
7. Still, W. C.; Novack, V. J. J. Am. Chem. Soc. 1984, 106, 1148-1149 and references cited therein.
8. Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943-2944.
9. Diastereoselective carbomagnesation: (a) Hoveyda, A. H.; Xu, Z. J. Am. Chem. Soc. 1991, 113, 5079-5080. (b) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. Enantioselective carbomagnesation: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298.
10. Diastereoselective carbomagnesation: (a) Hoveyda, A. H.; Xu, Z. J. Am. Chem. Soc. 1991, 113, 5079-5080. (b) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. Enantioselective carbomagnesation: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298.
11. Diastereoselective carbomagnesation: (a) Hoveyda, A. H.; Xu, Z. J. Am. Chem. Soc. 1991, 113, 5079-5080. (b) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. Enantioselective carbomagnesation: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298.
12. Diastereoselective carbomagnesation: (a) Hoveyda, A. H.; Xu, Z. J. Am. Chem. Soc. 1991, 113, 5079-5080. (b) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. Enantioselective carbomagnesation: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298.
13. Xu, D.; Crispino, G.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114. 7570-7571.
14. DeShong, P.; Dicken, C. M.; Leginus, J. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 5598-5602.
15. For the preparation of the requisite chiral hydroxylamine, see: Polonski, T.; Chimiak, A. Tetrahedron Lett. 1974, 2453-2456.
16. At this point, the diastereomer derived from minor dihydroxylation enantiomer is separated from 3b.
17. For the use of this chiral auxiliary in stereoselective reactions with O-silylketene acetals, see: Kita, Y.; Itoh, F.; Tamura, O.; Ke, Y. Y.; Tamura, Y. Tetrahedron Lett. 1987, 28, 1431-1434.
18. This experiment was carried out by Mr. Daniel La of these laboratories.
19. Imazawa, M.; Eckstein, F. J. Org. Chem. 1979, 44, 2039-2041.
20. Pozsgay, V. J. Am. Chem. Soc. 1995, 117, 6673-6681. Although the secondary amine of the unmasked carbohydrate (product of hydrogenation) could be protected, attempts to acylate the two secondary carbinols and the hemiacetal hydroxyl group, under a variety of conditions, led to the formation of complex mixtures of products.
21. Nicolaou, K. C.; Randall, J. L.; Furst, G. T. J. Am. Chem. Soc. 1985, 107, 5556-5558.
22. (a) Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 431-432.
23. (b) Mukaiyama, T.; Hashimoto, Y.; Shoda, S. Chem. Lett. 1983, 935-938.
24. (c) Nicolaou, K. C.; Dolle, R. E.; Papahatjis, D. P.; Randall, J. L.; J. Am. Chem. Soc. 1984, 106, 4189-4192.
25. Reference 14.
26. (a) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324-7325.
27. (b) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800-3801.
28. (c) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452 and references cited therein.
29. (d) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 107, 1981-1984 and references cited therein.
30. (e) Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875-3886.
31. (f) Bazan, G. C.; Schrock, R. R.; Cho, H.-N.; Gibson, V. C. Macromolecules 1991, 24, 4495-4502.
32. For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
33. For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
34. For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
35. For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
36. For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
37. For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
38. For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
39. Efforts to prepare more soluble derivatives of the macrolactam alcohol (e.g., the derived TMS ether) which would also be suitable for glycosylation by other methods (e.g., involving triacetate 7) were not successful. For an example, see: Mukaiyama, T.; Katsurada, M.; Takashima, T. Chem. Lett. 1991, 985-988.