Syntheses of 2-pyrones via electrophilic substitutions at C7 of 4-hydroxy-6-methyl-2-pyrone through mono- or dianion formation

Synthesis

Volumn , Issue 5, 2007, Pages 749-753

  Zhang, Xuejun ^a   McLaughlin, Michael ^a   Muñoz, R Lizeth P ^a   Hsung, Richard P ^a   Wang, Jiashi ^a   Swidorski, Jacob ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

2 pyrones; 4 hydroxy 6 methyl 2 pyrone; Dianion; Electrophilic substitution; Triacetic acid

Indexed keywords

2-PYRONES; 4-HYDROXY-6-METHYL-2-PYRONE; ELECTROPHILIC SUBSTITUTION; TRIACETIC ACID;

ACETIC ACID; NEGATIVE IONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

KETONES;

2 PYRONE DERIVATIVE; 4 HYDROXY 6 METHYL 2 PYRONE; ACETIC ACID DERIVATIVE; ANNULARIN E; ANTIINFECTIVE AGENT; TRIACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; SUBSTITUTION REACTION;

EID: 33947603718     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965925     Document Type: Article

References (38)

1. For a review, see: Romines, K. R.; Chrusciel, R. A. Curr. Med. Chem. 1995, 2, 825.
2. For recent reports, see: (a) Fors, K. S.; Gage, J. R.; Heier, R. F.; Kelly, R. C.; Perrault, W. R.; Wicnienski, N. J. Org. Chem. 1998, 63, 7348.
3. (b) Vara Prasad, J. V. N.; Tummino, P. J.; Ferguson, D.; Saunders, J.; Vander Roest, S.; McQuade, T. J.; Heldsinger, A.; Reyner, E. L.; Stewart, B. H.; Guttendorf, R. J.; Para, K. S.; Lunney, E. A.; Gracheck, S. J.; Domagala, J. M. Biochem. Biophys. Res. Commun. 1996, 221, 815.
4. (a) Schwartz, T. M.; Bundy, G. L.; Strohbach, J. W.; Thaisrivongs, S.; Johnson, P. D.; Skulnick, H. I.; Tomich, P. K.; Lynn, J. C.; Chong, K.-T.; Hinshaw, R. R.; Raub, T. J.; Padbury, G. E.; Toth, L. N. Bioorg. Med. Chem. Lett. 1997, 7, 399.
5. (b) Thaisrivongs, S.; Janakiraman, M. N.; Chong, K.-T.; Tomich, P. K.; Dolak, L. A.; Turner, S. R.; Strohbach, J. W.; Lynn, J. C.; Horng, M.-M.; Hinshaw, R. R.; Watenpaugh, K. D. J. Med. Chem. 1996, 39, 2400.
6. (c) Thaisrivongs, S.; Watenpaugh, K. D.; Howe, W. J.; Tomich, P. K.; Dolak, L. A.; Chong, K.-T.; Tomich, C. S. C.; Tomasselli, A. G.; Turner, S. R.; Strohbach, J. W.; Mulichak, A. M.; Janakiraman, M. N.; Moon, J. B.; Lynn, J. C.; Horng, M.-M.; Hinshaw, R. R.; Curry, K. A.; Rothrock, D. J. J. Med. Chem. 1995, 38, 3624.
7. For isolation, see: Shu, Y.-Z.; Ye, Q.; Li, H.; Kadow, K. F.; Hussain, R. A.; Huang, S.; Gustavson, D. R.; Lowe, S. E.; Chang, L. P.; Pirnik, D. M.; Kodukula, K. Bioorg. Med. Chem. Lett. 1997, 7, 2295.
8. For recent synthetic efforts toward orevactaene, see: (a) Organ, M. G.; Bratovanov, S. Tetrahedron Lett. 2000, 41, 6945.
9. (b) Organ, M. G.; Bilokin, Y. V.; Bratovanov, S. J. Org. Chem. 2002, 67, 5176.
10. For isolation, see: (a) Otoguro, K.; Kuno, F.; Õmura, S. Pharmacol. Ther. 1997, 76, 45.
11. (b) Otoguro, K.; Shiomi, K.; Yamaguchi, Y.; Arai, N.; Sunazuka, T.; Masuma, R.; Iwai, Y.; Õmura, S. J. Antibiot. 2000, 53, 5.
12. For a recent review on synthetic efforts toward arisugacin A, see: Cole, K. P.; Hsung, R. P. In Strategies and Tactics in Organic Synthesis, Vol.4; Harmata, M., Ed.; Pergamon Press: Oxford, 2004, 41-70.
13. For our total synthesis efforts, see: (a) Hsung, R. P. J. Org. Chem. 1997, 62, 7904.
14. (b) Zehnder, L. R.; Hsung, R. P.; Wang, J.-S.; Golding, G. M. Angew. Chem. Int. Ed. 2000, 39, 3876.
15. (c) Cole, K. P.; Hsung, R. P. Tetrahedron Lett. 2002, 43, 8791.
16. (d) Cole, K. P.; Hsung, R. P.; Yang, X.-F. Tetrahedron Lett. 2002, 43, 3341.
17. (e) Hsung, R. P.; Cole, K. P.; Zehnder, L. R.; Wang, J.; Wei, L. L.; Yang, X.-F.; Coverdale, H. A. Tetrahedron 2003, 59, 311.
18. For isolation, see: (a) Nair, M. S. R.; Carey, S. T. Tetrahedron Lett. 1975, 16, 3617.
19. (b) Nair, M. S. R. Phytochemistry 1976, 15, 1090.
20. Shimizu, T.; Hiranuma, S.; Wantanabe, T. Heterocycles 1993, 36, 2445.
21. For a leading reference, see: Katritzky, A. R.; Wang, Z.; Wang, M.; Hall, C. D.; Suzuki, K. J. Org. Chem. 2005, 70, 4854.
22. For some examples, see: (a) Organ, M. G.; Wang, J. J. Org. Chem. 2003, 68, 5568.
23. (b) Hagiwara, H.; Kobayashi, K.; Hoshi, T.; Suzuki, T.; Ando, M. Tetrahedron 2001, 57, 5039.
24. (c) Lokot, I. P.; Pashkovsky, F. S.; Lakhvich, F. A. Tetrahedron 1999, 55, 4783.
25. Douglas, C. J.; Sklenicka, H. M.; Shen, H. C.; Golding, G. M.; Mathias, D. S.; Degen, S. J.; Morgan, C. D.; Shih, R. A.; Mueller, K. L.; Seurer, L. M.; Johnson, E. W.; Hsung, R. P. Tetrahedron 1999, 55, 13683.
26. (a) For an earlier report on generating the dianion from triacetic acid, see: Wachter, M. P.; Harris, T. M. Tetrahedron 1970, 26, 1685.
27. For C7 alkylations, see: (b) Shimo, T.; Matsuzaki, S.; Somekawa, K. J. Heterocycl. Chem. 1994, 31, 387.
28. (c) Groutas, W. C.; Stanga, M. A.; Brubaker, M. J.; Huang, T. L.; Moi, M. K.; Carroll, R. T. J. Med. Chem. 1985, 28, 1106.
29. (d) Poulton, G. A.; Cyr, T. D. Can. J. Chem. 1982, 60, 2821.
30. For an addition to aldehyde, see: (e) Oikawa, H.; Kobayashi, T.; Katayama, K.; Suzuki, Y.; Ichihara, A. J. Org. Chem. 1998, 63, 8748.
31. For C7 oxidation, see: (f) Suzuki, E.; Hamajima, R.; Inoue, S. Synthesis 1975, 192.
32. (g) Bacardit, R.; Moreno-Mañas, M.; Pleixats, R. J. Heterocycl. Chem. 1982, 19, 157.
33. For bromination, see: (h) Jones, R. C. F.; Patience, J. M. Tetrahedron Lett. 1989, 30, 3217.
34. For an application of its utility, see: McLaughlin, M. J.; Hsung, R. P.; Cole, K. C.; Hahn, J. M.; Wang, J. Org. Lett. 2002, 4, 2017.
35. Li, C.; Nitka, M. V.; Gloer, J. B. J. Nat. Prod. 2003, 66, 1302.
36. For some other recently isolated related 2-pyrone containing natural products, see: (a) Cutignano, A.; Fontana, A.; Renzulli, L.; Cimino, G. J. Nat. Prod. 2003, 66, 1399.
37. (b) Pedras, M. S. C.; Chumala, P. B. Phytochemistry 2005, 66, 81.
38. For an application of its utility, see: Swidorski, J. J.; Wang, J.; Hsung, R. P. Org. Lett. 2006, 8, 777.