Conjugate addition of trimethylsilylmethyl cuprates to artemisinic acid: Homologation and subsequent conversion to 9β-modified artemisinin analogs

Synlett

Volumn , Issue 12, 1997, Pages 1438-1440

  Vroman, Jeffrey A ^a   Khan, Iklas ^b   Avery, Mitchell A ^b  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002611089     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1065     Document Type: Article

References (32)

1. Klayman, D. L. Science 1985, 228, 1049-55.
2. Luo, X.-D. and Shen, C.-C. Medical Research Reviews 1987, 7, 29-52.
3. Zhou, W.-S. and Xu, X.-X. Acc. Chem. Res. 1994, 27, 211-216.
4. Zaman, S. S. and Sharma, R. P. Heterocycles 1991, 32:, 1593-1638.
5. Jung, M. Curr. Med. Chem. 1994, 1, 35-49.
6. Avery, M. A.; Gao, F.; Mehrotra, S.; Chong, W. K. and Jennings-White, C. The Organic and Medicinal Chemistry of Artemisinin and Analogs. 1993, Trivandrum, India, Research Trends.
7. Butler, A. R. and Wu, Y. L. Chem. Soc. Reviews 1992, 21, 85-90.
8. Avery, M. A.; Chong, W. K. M.; and Jennings-White, C. J. Am. Chem. Soc. 1992, 114, 974-979.
9. Chinese Cooperative Research Group, J. Trad. Chinese Med. 1982, 2, 31-50.
10. Brewer, T. G.; Peggins, J. O.; Grate, S. J.; Petras, J. M.; Levine, B. S.; Weina, P. J.; Swearengen, J.; Heiffer, M. H. and Schuster, B. G. Trans. R. Soc. Trop. Med. Hyg. 1994, 88, 33-36.
11. Brewer, T. G.; Grate, S. J.; Peggins, J. O.; Weina, P. J.; Petras, J. M.; Levine, B. S.; Heiffer, M. H. and Schuster, B. G. Am. J. Trop. Med. Hyg. 1994, 51, 251-259.
12. Tregova, A.; Holme, A.D.; Bell, J.O.; McLean, W.G.; Edwards, G.; Ward, S.A. Br J. Pharmacol. 1997, 119, 336.
13. Smith, S.; Fishwick, J.; McLean, W.G.; Edwards, G.; and Ward, S.A. Biochem. Phannacol. 1996, 53, 5-10.
14. Avery, M. A.; Mehrotra, S., Johnson, T. L., Bonk, J. D., Vroman, J. A. and Miller, R. J. Med. Chem. 1996, 39, 4149-4155.
15. Haynes, R.K. and Vonwiller, S.C. Acc. Chem. Res. 1997, 30, 73-79.
16. Rossiter, B. E. and Swingle, N. M. Chem. Rev. 1992, 92, 771-806.
17. Cooke, M. P. Jr. J. Org. Chem. 1983, 48, 744-746.
18. Yamamoto, Y. and Maruyama, K. J. Am. Chem. Soc. 1978, 100, 3240-3241.
19. Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y. and Maruyama, K. J. Org. Chem. 1982, 47, 119-126.
20. Cooke, M. P. Jr. J. Org. Chem. 1987, 52, 5729-5733.
21. Perich, J. W. and Johns, R. B. Synthesis 1989, 701-702.
22. Bhide, R. S.; Levison, B. S.; Sharma, R. B.; Ghosh, S. and Salomon, R. G. Tetrahedrom Lett. 1986, 27, 671-674.
23. Wissner, A. and Grudzinskas, C. V. J. Org. Chem. 1978, 42, 3972-3974.
24. Aizpurua, J. M.; Cossio, F. P. and Palomo, C. J. Org. Chem. 1986, 51, 4941-4943.
25. Bertz, S. H.; Eriksson, M.; Miao, G. and Snyder, J. P. J. Am. Chem. Soc. 1996, 118, 10906-10907.
26. Jarvis, J. A.; Pearce, R. and Lappert, M. F. J. Chem. Soc., Dalton Trans. 1977, 999-1003.
27. Fleming, I.; Rowley, M.; Cuadrado, P.; Gonzalez-Nogal, A. M. and Pulido, F.J. Tetrahedron. 1989, 45, 413-424.
28. Matsuzawa, S.; Horiguchi, Y.; Makamura, E. and Kuwajima, I. Tetrahedron. 1989, 45, 349-362.
29. Bertz, S. H.; Miao, G.; Rossiter, B. E. and Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11023-11024.
30. Ahn, K. -H.; Klassen, R. B. and Lippard, S. J. Organometallics 1990, 9, 3178-3181.
31. 14,32 Known quantities from each run of dried, crude reaction product were then analyzed by HPLC and the yield and isomer ratios were quantitated relative to controls. In two examples, isolated yields (silica gel flash chromatography, 20% EtOAc/hexane) were determined in order to validate the HPLC method (Table I and II). All compounds displayed satisfactory spectral and analytical data.
32. Avery, M. A.; Fenglan, G.; Chong, W. K. M.; Mehrotra, S. and Milhous, W. K. J. Med. Chem. 1993, 36, 4264-4275.