An expedient approach to the 2,3,5,6-tetrasubstituted pyridine core of nosiheptide using oxidative cleavage of 2,3,5,8-tetrasubstituted quinolines

Arkivoc

Volumn 2007, Issue 11, 2007, Pages 56-63

  Taddei, David ^a   Poriel, Cyril ^b   Moody, Christopher J ^a,b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

Ozonolysis; Pyridine; Quinoline

Indexed keywords

EID: 33846322546     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.b05     Document Type: Article

References (32)

1. Bagley, M. C.; Dale, J. W.; Merritt, E. A.; Xiong, X.; Chem. Rev. 2005, 105, 685.
2. Shimanaka, K.; Kinoshita, N.; Iinuma, H.; Hamada, M.; Takeuchi, T.; J. Antibiotics 1994, 47, 668.
3. Clough, B.; Strath, M.; Preiser, P.; Denny, P.; Wilson, R. J. M.; FEBS Lett. 1997, 406, 123.
4. (a) Xing, Y. Y.; Draper, D. E.; Biochemistry 1996, 35, 1581.
5. (b) Heffron, S. E.; Jurnak, F.; Biochemistry 2000, 39, 37.
6. Synthetic efforts have focused on the Bycroft-Gowland proposed structure of micrococcin P1, which has since been revised by Bagley and Merritt. Hence, the NMR spectra of synthetic micrococcin samples have not been found identical to those of the natural product; Shin, C.-G.; Okumura, K.; Shigekuni, M.; Nakamura, Y.; Chem. Lett. 1998, 139.
7. Okumura, K.; Nakamura, Y.; Shin, C.; Bull. Chem. Soc. Jpn. 1999, 72, 1561.
8. Okumura, K.; Ito, A.; Yoshioka, D.; Shin, C.-G.; Heterocycles 1998, 48, 1319.
9. Okumura, K.; Suzuki, T.; Nakamura, Y.; Shin, C.-G.; Bull. Chem. Soc. Jpn. 1999, 72, 2483.
10. Ciufolini, M. A.; Shen, Y.-C.; Org. Lett. 1999, 1, 1843.
11. Bagley, M.C.; Merritt, E. A.; J. Antibiot. 2004, 57, 829.
12. (a) Nicolaou, K. C.; Safina, B. S.; Zak, M.; Lee, S. H.; Nevalainen, M.; Bella, M.; Estrada, A. A.; Funke, C.; Zecri, F. J.; Bulat, S.; J. Am. Chem. Soc. 2005, 127, 11159.
13. (b) Nicolaou, K. C.; Zak, M.; Safina, B. F.; Estrada, A. A.; Lee, S. H.; Nevalainen, M.; J. Am. Chem. Soc. 2005, 127, 11176.
14. Bagley, M. C.; Bashford, K. E.; Hesketh, C. L.; Moody, C. J.; J. Am. Chem. Soc. 2000, 122, 3301.
15. Hughes, R. A.; Thompson, S. P.; Alcaraz, L.; Moody, C. J.; J. Am. Chem. Soc. 2005, 127, 15644.
16. Koerber-Plé, K.; Massiot, G.; Synlett 1994, 759.
17. Shin, C.; Nakamura, Y.; Yamada, Y.; Yonezawa, Y.; Umemura, K.; Yoshimura, J.; Bull. Chem. Soc. Jpn. 1995, 68, 3151.
18. Koerber-Plé, K.; Massiot, G. ; J. Heterocycl. Chem. 1995, 32, 1309.
19. Umemura, K.; Tate, T.; Yamaura, M.; Yoshimura, J.; Yonezawa, Y.; Shin, C. ; Synthesis 1995, 1423.
20. Shin, C.; Yamada, Y.; Hayashi, K.; Yonezawa, Y.; Umemura, K.; Tanji, T.; Yoshimura, J.; Heterocycles 1996, 43, 891.
21. Umemura, K.; Noda, H.; Yoshimura, J.; Konn, A.; Yonezawa, Y.; Shin, C. G.; Tetrahedron Lett. 1997, 38, 3539.
22. Umemura, K.; Noda, H.; Yoshimura, J.; Konn, A.; Yonezawa, Y.; Shin, C. G., Bull. Chem. Soc. Jpn. 1998, 71, 1391.
23. Ciufolini, M. A.; Shen, Y. C.; J. Org. Chem. 1997, 62, 3804.
24. Heckmann, G.; Bach, T.; Angew. Chem., Int. Ed. 2005, 44, 1199.
25. Moody, C. J.; Hughes, R. A.; Thompson, S. P.; Alcaraz, L.; Chem. Commun. 2002, 1760.
26. (a) Bohlmann, F.; Rahtz, D.; Chem. Ber. 1957, 90, 2265.
27. (b) Bagley, M. C.; Chapaneri, K.; Dale, J. W.; Xiong, X.; Bower, J.; J. Org. Chem. 2005, 70, 1389.
28. (c) Bagley, M. C.; Dale, J. W.; Ohnesorge, M.; Xiong, X.; Bower, J.; J. Comb. Chem. 2003, 5, 41.
29. Le Bas, M.-D.; Guéret, C; Perrio, C ; Lasne, M.-C. ; Barré, L ; Synthesis 2001, 2495.
30. (a) Meth-Cohn, O.; Narine, B.; Tarnowski, B.; Tetrahedron Lett. 1979, 33, 3111.
31. (b) Meth-Cohn, O.; Narine, B.; Tarnowski, B.; J. Chem. Soc., Perkin Trans. 1 1981, 1520.
32. Akhavan-Tafti, H.; DeSilva, R.; Arghavani, Z.; Eickholt, R. A.; Handley, R. S.; Schoenfelner, B. A.; Sugioka, K.; Sugioka, Y.; Schaapet, A. P.; J. Org. Chem., 1998, 63, 930.