Asymmetric synthesis of the putative structure of (-)-oryzoxymycin

Organic Letters

Volumn 5, Issue 3, 2003, Pages 239-242

  Bunnage, Mark E ^b   Ganesh, Thota ^a   Masesane, Ishmael B ^a   Orton, Darren ^a   Steel, Patrick G ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2' (6 AMINO 5 HYDROXY 1,3 CYCLOHEXADIENE 1 CARBONYLOXY)PROPIONIC ACID; ANTIBIOTIC AGENT; ORYZOXYMYCIN; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; CYCLOHEXANECARBOXYLIC ACID DERIVATIVE; CYCLOHEXENE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; CHEMISTRY; SYNTHESIS;

CYCLOHEXANECARBOXYLIC ACIDS; CYCLOHEXENES; MOLECULAR STRUCTURE;

EID: 0013164731     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0269704     Document Type: Article

References (28)

1. Hashimoto, T.; Kondo, S.; Takita, T.; Hamada, M.; Takeuchi, T.; Okami, Y.; Umezawa, H. J. Antibiot. 1968, 21, 653-658.
2. Hashimoto, T.; Takahashi, S.; Naganawa, H.; Takita, T.; Maeda, K.; Umezawa, H. J. Antibiot. 1972, 25, 350-355.
3. Hashimoto, T.; Kondo, S.; Naganawa, H.; Takita, T.; Maeda, K.; Umezawa, H. J. Antibiot. 1974, 27, 86-87.
4. Walsh, C. T.; Erion, M. D.; Walts, A. E.; Delany, J. J.; Berchtold, G. A. Biochemistry 1987, 26, 4734-4745.
5. Morollo, A. A.; Finn, M. G.; Bauerle, R. J. Am. Chem. Soc. 1993, 115, 5, 816-817.
6. Anderson, K. S.; Kati, W. M.; Ye, C. Z.; Liu, J.; Walsh, C. T.; Benesi, A. J.; Johnson, K. A. J. Am. Chem. Soc. 1991, 113, 3198-3200.
7. For a recent review of this field, see: Fülöp, F. Chem. Rev. 2001, 101, 2181-2204.
8. See, for example: (a) Teng, C. Y. P.; Ganem, B.; Doktor, S. Z.; Nichols, B. P.; Bhatnagar, R. K.; Vining, L. C. J. Am. Chem. Soc. 1985, 107, 5008-5009. (b) Teng, C. Y. P.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 2463-2464. (c) Policastro, P. P.; Au, K. G.; Walsh, C. T.; Berchtold, G. A. J. Am. Chem. Soc. 1984, 106, 2443-2444. (d) Kozlowski, M. C.; Tom, N. J.; Seto, C. T.; Sefler, A. M.; Bartlett, P. A. J. Am. Chem. Soc. 1995, 117, 2128-2140.
9. See, for example: (a) Teng, C. Y. P.; Ganem, B.; Doktor, S. Z.; Nichols, B. P.; Bhatnagar, R. K.; Vining, L. C. J. Am. Chem. Soc. 1985, 107, 5008-5009. (b) Teng, C. Y. P.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 2463-2464. (c) Policastro, P. P.; Au, K. G.; Walsh, C. T.; Berchtold, G. A. J. Am. Chem. Soc. 1984, 106, 2443-2444. (d) Kozlowski, M. C.; Tom, N. J.; Seto, C. T.; Sefler, A. M.; Bartlett, P. A. J. Am. Chem. Soc. 1995, 117, 2128-2140.
10. See, for example: (a) Teng, C. Y. P.; Ganem, B.; Doktor, S. Z.; Nichols, B. P.; Bhatnagar, R. K.; Vining, L. C. J. Am. Chem. Soc. 1985, 107, 5008-5009. (b) Teng, C. Y. P.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 2463-2464. (c) Policastro, P. P.; Au, K. G.; Walsh, C. T.; Berchtold, G. A. J. Am. Chem. Soc. 1984, 106, 2443-2444. (d) Kozlowski, M. C.; Tom, N. J.; Seto, C. T.; Sefler, A. M.; Bartlett, P. A. J. Am. Chem. Soc. 1995, 117, 2128-2140.
11. See, for example: (a) Teng, C. Y. P.; Ganem, B.; Doktor, S. Z.; Nichols, B. P.; Bhatnagar, R. K.; Vining, L. C. J. Am. Chem. Soc. 1985, 107, 5008-5009. (b) Teng, C. Y. P.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 2463-2464. (c) Policastro, P. P.; Au, K. G.; Walsh, C. T.; Berchtold, G. A. J. Am. Chem. Soc. 1984, 106, 2443-2444. (d) Kozlowski, M. C.; Tom, N. J.; Seto, C. T.; Sefler, A. M.; Bartlett, P. A. J. Am. Chem. Soc. 1995, 117, 2128-2140.
12. Enantiomerically pure DHAA has been isolated from a fermantation culture (McCormick, J. R. D.; Reichenthal, J.; Hirsch, U.; Sjolander, N. O. J. Am. Chem. Soc. 1962, 84, 3711) and subsequently used in asymmetric syntheses of related structures; see ref 8b. For an alternative approach to DHAA, see: Fukuyama, T.; Nakatsuka, S.; Kishi, Y. Tetrahedron 1981, 37, 2045-2078 references therein.
13. Enantiomerically pure DHAA has been isolated from a fermantation culture (McCormick, J. R. D.; Reichenthal, J.; Hirsch, U.; Sjolander, N. O. J. Am. Chem. Soc. 1962, 84, 3711) and subsequently used in asymmetric syntheses of related structures; see ref 8b. For an alternative approach to DHAA, see: Fukuyama, T.; Nakatsuka, S.; Kishi, Y. Tetrahedron 1981, 37, 2045-2078 references therein.
14. Just, G.; Martel, A. Tetrahedron Lett. 1973, 1517-1520.
15. McMurry, J. E.; Musser, J. H. Org. Synth. 1977, 56, 65-68.
16. Jew, S. S.; Kim, H. D.; Cho, Y. S.; Cook, C. H. Chem. Lett. 1986, 1747-1748.
17. Itoh, K.; Kitoh, K.; Sera, A. Heterocycles 1999, 51, 243-248.
18. (a) Brion, F. Tetrahedron Lett. 1982, 23, 5299-5302.
19. (b) Rajapaksa, D.; Keay, B. A.; Rodrigo, R. Can. J. Chem. 1984, 62, 826-827.
20. (c) Campbell, M. M.; Sainsbury, M.; Searle, P. A. Synthesis 1993, 179-193.
21. (d) Evans, D. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 57-58 and references therein.
22. Similar observations have been noted elsewhere. See, for example, ref 8d and: Couche, E.; Deschatrettes, R.; Poumellec, K.; Bortolussi, M.; Mandville, G.; Bloch, R. Synlett 1999, 87-89.
23. The relatively high stability of the free hydroxy compound relative to substituted analogues has been noted in similar systems and can be attributed to a conformational effect that places both heteroatom substituent in a different plane to both the diene p-system and the neighboring H atoms. For similar observations, see ref 8d.
24. Otera, J.; Nakazawa, K.; Sekoguchi, K.; Orita, A. Tetrahedron 1997, 53, 13633-13640.
25. Nitroacrylates bearing chiral auxiliaries have been successfully prepared and used in asymmetric Diels-Alder reactions. See: Clive, D. L. J.; Bo, Y. X.; Selvakumar, N.; McDonald, R.; Santarsiero, B. D. Tetrahedron 1999, 55, 3277-3290.
26. See, for example: Bloch, R.; Guibejampel, E.; Girard, C. Tetrahedron Lett. 1985, 26, 4087-4090. Schueller, C. M.; Manning, D. D.; Kiessling, L. L. Tetrahedron Lett. 1996, 37, 8853-8856 and references therein.
27. See, for example: Bloch, R.; Guibejampel, E.; Girard, C. Tetrahedron Lett. 1985, 26, 4087-4090. Schueller, C. M.; Manning, D. D.; Kiessling, L. L. Tetrahedron Lett. 1996, 37, 8853-8856 and references therein.
28. -1.