Synthesis of the spiroketal segment (C19-C34) of the rutamycins, antifungal metabolites of streptomyces species

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3167-3170

  White, James D ^a   Ohba, Yoshihiro ^a   Porter, Warren J ^a   Wang, Shan ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; RUTAMYCIN;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030948504     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00585-6     Document Type: Article

References (22)

1. (a) Thompson, R. Q.; Hoehn, M. M.; Higgins, C. E. Antimicrob. Agents Chemother. 1961, 474.
2. (b) Arnoux, B.; Garcia-Alvarez, M. C.; Marazano, C.; Bhupesh, C. D.; Pascard, C. J. Chem. Soc., Chem. Commun. 1978, 318.
3. Wuthier, D.; Keller-Schierlein, W.; Wahl, B. Helv. Chim. Acta 1984, 67, 1208.
4. Nakagawa, A.; Miura, S.; Imai, H.; Imamura, N.; Omura, S. J. Antibiot. 1989, 42, 1324.
5. Kihara, T.; Kusakabe, H.; Nakamura, G.; Sakurai, T.; Isono, K. J. Antibiot. 1981, 34, 1073.
6. (a) Smith, R. M.; Peterson, W. H.; McCoy, E. Antibiot. Chemother. 1954, 4, 962.
7. (b) Kobayashi, K.; Nishino, C.; Ohya, J.; Sato, S.; Shiobara, Y.; Kodama, M.; Nishimoto, N. J. Antibiot. 1987, 40, 1053.
8. For synthesis of the "northern" polypropionate (C1-C15) segment of 2, see White, J. D.; Porter, W. J.; Tiller, T. Synlett. 1993, 535; for the total synthesis of rutamycin B, see Evans, D. A.; Ng, H. P.; Rieger, D. L. J. Am. Chem. Soc. 1993, 125, 11446.
9. For synthesis of the "northern" polypropionate (C1-C15) segment of 2, see White, J. D.; Porter, W. J.; Tiller, T. Synlett. 1993, 535; for the total synthesis of rutamycin B, see Evans, D. A.; Ng, H. P.; Rieger, D. L. J. Am. Chem. Soc. 1993, 125, 11446.
10. For precedent along these lines, see Evans, D. A.; Rieger, D. L.; Jones, T. K.; Kaldor, S. W. J. Org. Chem. 1990, 55, 6260.
11. Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348.
12. Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570.
13. Tsuji, J. Synthesis 1984, 369.
14. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
15. Corey, E. J.; Hopkins, P. B. Tetrahedron Lett. 1982, 23, 4871.
16. Castro, B.R. Org. React. 1983, 29, 1.
17. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 83.
18. Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047.
19. Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339.
20. Julia, M. Pure Appl. Chem. 1985, 57, 763.
21. Ley, S.V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
22. Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 57, 1135.