Efficient stereoselective synthesis of the epoxyacid fragment of the azinomycins

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 5917-5920

  Coleman, Robert S ^a   Sarko, Christopher R ^b   Gittinger, Jens P ^b  

^a OHIO STATE UNIVERSITY   (United States)

^b UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ANTINEOPLASTIC ANTIBIOTIC; AZINOMYCIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030744310     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01322-1     Document Type: Article

References (37)

1. Nagaoka, K.; Matsumoto, M.; Oono, J.; Yokoi, K.; Ishizeki, S.; Nakashima, T. J. Antibiot. 1986, 39, 1527. Yokoi, K.; Nagaoka, K.; Nakashima, T. Chem. Pharm. Bull. 1986, 34, 4554.
2. Nagaoka, K.; Matsumoto, M.; Oono, J.; Yokoi, K.; Ishizeki, S.; Nakashima, T. J. Antibiot. 1986, 39, 1527. Yokoi, K.; Nagaoka, K.; Nakashima, T. Chem. Pharm. Bull. 1986, 34, 4554.
3. 5a, m that azinomycin B is identical to carzinophilin A, an antitumor agent isolated from Streptomyces sahachiroi. Hata, T.; Koga, F.; Sano, Y.; Kanamori, K.; Matsumae, A.; Sugawara, R.; Hoshi, T.; Shimi, T.; Ito, S.; Tomizawa, S. J. Antibiot. Ser. A. 1954, 7,107.
4. Ishizeki, S.; Ohtsuka, M.; Irinoda, K.; Kukita, K.-I.; Nagaoka, K.; Nakashima, T. J. Antibiot. 1987, 40, 60.
5. Terawaki, A.; Greenberg, J. Nature 1966, 209, 481. Lown, J. W.; Majumdar, K. C. Can. J. Biochem. 1977, 55,630. Armstrong, R. W.; Salvati, M. E.; Nguyen, M. J. Am. Chem. Soc. 1992, 114, 3144.
6. Terawaki, A.; Greenberg, J. Nature 1966, 209, 481. Lown, J. W.; Majumdar, K. C. Can. J. Biochem. 1977, 55,630. Armstrong, R. W.; Salvati, M. E.; Nguyen, M. J. Am. Chem. Soc. 1992, 114, 3144.
7. Terawaki, A.; Greenberg, J. Nature 1966, 209, 481. Lown, J. W.; Majumdar, K. C. Can. J. Biochem. 1977, 55,630. Armstrong, R. W.; Salvati, M. E.; Nguyen, M. J. Am. Chem. Soc. 1992, 114, 3144.
8. (a) Kondo, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y. Chem. Pharm. Bull. 1994, 42, 285.
9. (b) Ando, K.; Yamada, T.; Shibuya, M. Heterocycles 1989, 29, 2209.
10. (c) Shishido, K.; Omodani, T.; Shibuya, M. J. Chem. Soc., Perkin 1 1992, 2053.
11. (d) Shibuya, M.; Terauchi, H. Tetrahedron Lett. 1987,28, 2619.
12. (e) Shibuya, M. Tetrahedron Lett. 1983, 24, 1175.
13. (f) Hashimoto, M.; Terashima, S. Tetrahedron Lett. 1994, 35, 9409.
14. (g) Haahimoto, M.; Terashima, S. Chem. Lett. 1994, 35, 2207.
15. (h) Hashimoto, M.; Yamada, K.; Terashima, S. Chem. Lett. 1992, 33, 975.
16. (i) Moran, E. J.; Tellew, J. E.; Zhao, Z.; Armstrong, R. W. J. Org. Chem. 1993, 58, 7848.
17. (j) Armstrong, R. W.; Moran, E. J. J. Am. Chem. Soc. 1992, 114, 371.
18. (k) Combs, A. P.; Armstrong, R. W. Tetrahedron Lett. 1992,33, 6419.
19. (l) Armstrong, R. W.; Tellew, J. E.; Moran, E. J. J. Org. Chem. 1992, 57, 2208.
20. (m) Moran, E. J.; Armstrong, R. W. Tetrahedron Lett. 1991, 32, 3807.
21. (n) England, P.; Chun, K. H.; Moran, E. J.; Armstrong, R. W. Tetrahedron Lett. 1990, 31, 2669.
22. (o) Bryant, H. J.; Dardonville, C. Y.; Hodgkinson, T. J.; Shipman, M.; Slawin, A. M. Z. Synlett 1996, 973.
23. Coleman, R. S.; Carpenter, A. J. J. Org. Chem. 1992, 57, 5813.
24. Coleman, R. S.; Carpenter, A. J. J. Org. Chem. 1993, 58, 4452.
25. Coleman, R. S.; Carpenter, A. J. Tetrahedron 1997, 53, 0000.
26. 2S) followed by fractional bulb-to-bulb distillation to remove dimethylsulfoxide. Jung, M. E.; Shishido, K.; Davis, L. H. J. Org. Chem. 1982, 47, 891.
27. In earlier model studies, vinylmagnesium bromide was found to effect aldehyde reduction as the major reaction pathway.
28. Prepared from isopropenyl acetate and phenylselenyl chloride: Toshimitsu, A.; Aoai, T.; Owada, H.; Uemura, S.; Okano, M. J. Chem. Soc. Chem. Commun. 1980, 412.
29. Lerouge, P.; Paulmier, C. Bull. Chim. Soc. Fr. 1985, 1225.
30. Chunduru, S. K; Mrachko, G. T.; Calvo, K. C. Biochemistry 1989, 28, 486.
31. Yates, P.; Hoare, J. H. Can. J. Chem. 1983, 61, 1397.
32. Johnson, R. A.; Sharpless, K. B. in Comprehensive Organic Synthesis, Trost, B. M. and Ley, S. V., Eds.; Pergamon Press; vol. 7, p. 389; 1991. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
33. Johnson, R. A.; Sharpless, K. B. in Comprehensive Organic Synthesis, Trost, B. M. and Ley, S. V., Eds.; Pergamon Press; vol. 7, p. 389; 1991. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
34. 19F NMR using the corresponding Mosher ester.
35. For a similar effect, see: Luly, J. R.; Hsiao, C.-H.; BaMaung, N.; Plattner, J. J. J. Org. Chem. 1988, 53, 6109.
36. For examples of inverted enantioselectivity in Katsuki-Sharpless epoxidations resulting from the presence of both allylic and homoallylic hydroxyl groups, see: Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Am. Chem. Soc. 1991, 113, 2786. Takano, S.; Setoh, M.; Takahashi, M.; Ogasawara, K. Tetrahedron Lett. 1992, 33, 5365.
37. For examples of inverted enantioselectivity in Katsuki-Sharpless epoxidations resulting from the presence of both allylic and homoallylic hydroxyl groups, see: Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Am. Chem. Soc. 1991, 113, 2786. Takano, S.; Setoh, M.; Takahashi, M.; Ogasawara, K. Tetrahedron Lett. 1992, 33, 5365.