Synthesis of amphotericin B. A convergent strategy to the polyol segment of the heptaene macrolide antibiotics

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 5704-5705

  McGarvey, Glenn J ^a   Mathys, Jeffrey A ^a   Wilson, Kenneth J ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN B;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029801779     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9609337     Document Type: Article

References (24)

1. Omura, S.; Tanaka, H. In Macrolide Antibiotics: Chemistry, Biology, and Practice; Omura, S., Ed.; Academic Press: New York, 1984; pp 351-404. We refer to those structures that differ from a heptaene macrolide antibiotic (e.g., 1) by saturation at C28-C29 as pseudoheptaene macrolide antibiotics (e.g., 2).
2. Gallis, H. A.; Drew, R. H.; Pickard, W. W. Rev. Infect. Dis. 1990, 12, 308-329.
3. Brajtburg, J.; Powderly, W. G.; Kobayashi, G. S.; Medoff, G. Antimicrob. Agents Chemother. 1990, 34, 183-188.
4. For a review: Beau, J.-M. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990; pp 135-182.
5. Total synthesis of amphotericin B: (a) Nicolaou, K. C.; Ogilvie, W. W. Chemtracts-Org. Chem. 1990, 3, 327-349. 19-Dehydroamphoteronolide B: (b) Kennedy, R. M.; Abiko, A.; Takenasa, T.; Okumoto, H.; Masamune, S. Tetrahedron Lett. 1988, 29, 451-454.
6. Total synthesis of amphotericin B: (a) Nicolaou, K. C.; Ogilvie, W. W. Chemtracts-Org. Chem. 1990, 3, 327-349. 19-Dehydroamphoteronolide B: (b) Kennedy, R. M.; Abiko, A.; Takenasa, T.; Okumoto, H.; Masamune, S. Tetrahedron Lett. 1988, 29, 451-454.
7. For syntheses of nonheptaene macrolide antibiotics see the following. Mycoticin A: (a) Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360-3361. (+)-Roxaticin (natural): (b) Mori, Y.; Asai. M.; Okuraura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. (c) Mori, Y.; Asai. M.; Kawade, J.-i.; Furukawa, H. Tetrahedron 1995, 51, 5315-5330. (-)-Roxaticin (unnatural): (d) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. Pimarolide: (e) Duplantier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079-7081.
8. For syntheses of nonheptaene macrolide antibiotics see the following. Mycoticin A: (a) Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360-3361. (+)-Roxaticin (natural): (b) Mori, Y.; Asai. M.; Okuraura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. (c) Mori, Y.; Asai. M.; Kawade, J.-i.; Furukawa, H. Tetrahedron 1995, 51, 5315-5330. (-)-Roxaticin (unnatural): (d) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. Pimarolide: (e) Duplantier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079-7081.
9. For syntheses of nonheptaene macrolide antibiotics see the following. Mycoticin A: (a) Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360-3361. (+)-Roxaticin (natural): (b) Mori, Y.; Asai. M.; Okuraura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. (c) Mori, Y.; Asai. M.; Kawade, J.-i.; Furukawa, H. Tetrahedron 1995, 51, 5315-5330. (-)-Roxaticin (unnatural): (d) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. Pimarolide: (e) Duplantier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079-7081.
10. For syntheses of nonheptaene macrolide antibiotics see the following. Mycoticin A: (a) Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360-3361. (+)-Roxaticin (natural): (b) Mori, Y.; Asai. M.; Okuraura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. (c) Mori, Y.; Asai. M.; Kawade, J.-i.; Furukawa, H. Tetrahedron 1995, 51, 5315-5330. (-)-Roxaticin (unnatural): (d) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. Pimarolide: (e) Duplantier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079-7081.
11. For syntheses of nonheptaene macrolide antibiotics see the following. Mycoticin A: (a) Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360-3361. (+)-Roxaticin (natural): (b) Mori, Y.; Asai. M.; Okuraura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. (c) Mori, Y.; Asai. M.; Kawade, J.-i.; Furukawa, H. Tetrahedron 1995, 51, 5315-5330. (-)-Roxaticin (unnatural): (d) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. Pimarolide: (e) Duplantier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079-7081.
12. For previous studies in these laboratories: (a) McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943-4952. (b) McGarvey, G. J.; Mathys, J. A.; Wilson, K J.; Overly, K. R.; Buonora, P. T.; Spoors, P. G. J. Org. Chem. 1995, 60, 7778-7790.
13. For previous studies in these laboratories: (a) McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943-4952. (b) McGarvey, G. J.; Mathys, J. A.; Wilson, K J.; Overly, K. R.; Buonora, P. T.; Spoors, P. G. J. Org. Chem. 1995, 60, 7778-7790.
14. For a recent review. Easton, C. J.; Hughes, C. M. M.; Savage, G. P.; Simpson, G. W. Adv. Heterocycl. Chem. 1994, 60, 261-327.
15. Merifield, E.; Steele, P. G.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1987, 1826-1828.
16. Evans, D. A.; Sjogren, E. B.; Bartroli, J.; Dow, R. L. Tetrahedron Lett. 1986, 27, 4957-4960.
17. 2, 53%.
18. Moriya, O.; Tanenaka, H.; Iyoda, M.; Urata, Y.; Endo, T. J. Chem. Soc., Perkin Trans, 1 1994, 413-417.
19. tBuOCl.
20. 1H NMR.
21. Baraldi, P.; Barco, A.; Benetti, S.; Manfredini, S.; Simoni, D. Synthesis 1987, 276-278.
22. Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem. Pharm. Bull. 1981, 29, 1475-1478.
23. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156-4156.
24. Bal, B. S.; Childers, W. E.; Pinnick, H. W. Tetrahedron 1981, 37, 2091-2096.