On the susceptibility of organic peroxy bonds to hydride reduction

Journal of Organic Chemistry

Volumn 70, Issue 11, 2005, Pages 4240-4247

  Jin, Hong Xia ^a   Liu, He Hua ^a   Zhang, Qi ^a   Wu, Yikang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHEMICAL BONDS; ESTERS; HYDRIDES; PEROXIDES; REDUCTION; SYNTHESIS (CHEMICAL);

HYDRIDE REDUCTANTS; ORGANIC MOLECULES; PEROXY BONDS; PEROXY LINKAGE;

ORGANIC COMPOUNDS;

ALCOHOL; ESTER; HYDROGEN; LITHIUM DERIVATIVE; PEROXIDE; REDUCING AGENT;

ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; REDUCTION KINETICS; SYNTHESIS;

EID: 19544367275     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050139y     Document Type: Article

References (44)

1. (a) Cremer, D. In The Chemistry of Peroxides; Patai, S., Ed.; John Wiley & Sons: Chichester, U.K., 1983; Chapter 1, p 3.
2. (b) Davies, A. G. Organic Peroxides; Butterworth: London, 1961.
3. (c) In Organic Peroxides; Swern, D., Ed.; Wiley-Interscience: New York, 1970; Vol. 1-2.
4. (d) In Organic Peroxides; Swern, D., Ed.; Wiley-Interscience: New York, 1972; Vol. 3.
5. (e) In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: Chichester, 1983.
6. (a) Liu, J.-M.; Ni, M.-Y.; Tu, A.-A.; Wu, Z.-H.; Wu, Y.-L.; Zhou, W. S. (Hua Hsueh Hsueh Pao) Hua Xue Xue Bao (now often translated as Acta Chim. Sinica) 1979, 37, 129-143;
7. Chem. Abstr. 1979, 92, 94594.
8. (b) Li, Y.; Wu, Y.-L. Curr. Med. Chem. 2003, 10, 2197-2230 and the references therein.
9. Wu, Y.-L.; Zhang, J.-L. You Ji Hua Xue (now often translated as Chin. J. Org. Chem.) 1986, 154-156;
10. Chem. Abstr. 1986, 105, 191426n.
11. Jung, M.; Li, X.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D.; Milhous, W. K. J. Med. Chem. 1990, 33, 1516-1518.
12. (a) Avery, M. A.; Mehrotra, S.; Johnson, T. L.; Bonk, J. D.; Vroman, J. A.; Miller, R. J. Med. Chem. 1996, 39, 4149-4155.
13. (b) Avery, M. A.; Alvim-Gaston, M.; Vroman, J. A.; Wu, B.; Ager, A.; Peters, W.; Robinson, B.; Charman, W. J. Med. Chem. 2002, 45, 4321-4335.
14. Mekonnen, B.; Weiss, E.; Katz, E.; Ma, J.; Ziffer, H.; Kyle, D. Bioorg. Med. Chem. 2000, 8, 1111-1116.
15. Stierle, D. B.; Faulkner, D. J. J. Org. Chem. 1980, 45, 3396-3401.
16. Kobayashi, M.; Kondo, K.; Kitagawa, I. Chem. Phar, Bull. 1993, 41, 1324-1326.
17. (a) Quinoa, E.; Kho, E.; Manes, L. V.; Crews, P.; Bakus, G. J. J. Org. Chem. 1986, 51, 4260-4264.
18. (b) Braekman, J. C.; Daloze, D.; De Groote, S.; Fernandes, J. B.; Van Soest, R. W. M. J. Nat. Prod. 1998, 61, 1038-1042.
19. (c) Albericci, M.; Braekman, J. C.; Daloze, D.; Tursch, B. Tetrahedron 1982, 38, 1881-1890.
20. (d) Muellner, U.; Huefnerm, A.; Haslinger, E. Tetrahedron 2000, 56, 3893-3900.
21. Dussault, P.; Sahli, A.; Westermeyer, T. J. Org. Chem. 1993, 58, 5469-5474.
22. Porter, N. A.; Caldwell, S. E.; Lowe, J. R. J. Org. Chem. 1998, 63, 5547-5554.
23. (a) Xu, X.-X.; Zhu, J.; Huang, D.-Z.; Zhou, W.-S. Tetrahedron Lett. 1991, 32, 5785-5788.
24. (b) Vennerstrom, J. L.; Arbe-Barnes, S.; Brun, R.; Charman, S. A.; Chiu, F. C.; Chollet, J.; Dong, Y.; Dorn, A.; Hunziker, D.; Matile, H.; McIntosh, K.; Padmanilayam, M.; Santo Tomas, J.; Scheurer, C.; Scorneaux, B.; Tang, Y.; Urwyler, H.; Wittlin, S.; Charman, W. N. Nature 2004, 430, 900-904.
25. (c) O'Neill, P. M. Nature 2004, 430, 838-839.
26. (d) Tang, Y.; Dong, Y.; Karle, J. M.; DiTusa, C. A.; Vennerstrom, J. L. J. Org. Chem. 2004, 69, 6470-6473.
27. See: e. g., (a) Vennerstrom, J. L.; Arbe-Barnes, S.; Brun, R.; Charman, S. A.; Chiu, F. C.; Chollet, J.; Dong, Y.; Dorn, A.; Hunziker, D.; Matile, H.; McIntosh, K.; Padmanilayam, M.; Santo Tomas, J.; Scheurer, C.; Scorneaux, B.; Tang, Y.; Urwyler, H.; Wittlin, S.; Charman, W. N. Identification of an antimalarial synthetic trioxolane drug development candidate. Nature 2004, 430, 900-904.
28. (b) Tang, Y.; Dong, Y.; Vennerstrom, J. L. Synthetic peroxides as antimalarials. Med Res Rev. 2004, 24, 425-448.
29. (c) O'Neill, P. M. Medicinal chemistry: a worthy adversary for malaria. Nature 2004, 430, 838-839.
30. (d) Casteel, D. A. Peroxy Natural Products. Nat. Prod. Rev. 1992, 289-312.
31. See, e. g.,: (a) Malek, J.; Cerny, M. Synthesis 1972, 217-234.
32. (b) Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1464-1472.
33. Ayers, T. A. Tetrahedron Lett. 1999, 40, 5467-5470.
34. Guida, W. C.; Entreken, E. E.; Guida, A. R. J. Org. Chem. 1984, 49, 3024-3026.
35. (a) Jefford, C. W.; Jaber, A.; Boukouvalas, J. J. Chem. Soc. Chem. Commun. 1989, 1916-1917.
36. (b) Sels, B. F.; De Vos, D. E.; Grabet, P. J.; Pierard, F.; Kirsch-De Mesmaeker, F.; Jacobs, P. A. J. Phys. Chem. B 1999, 103, 11114.
37. (c) Posner, G. H.; Tao, X.-L.; Cumming, J. N.; Klinedinst, D.; Shapiro, T. A. Tetrahedron Lett. 1996, 37, 7225.
38. (d) Jin, H.-X.; Liu, H.-H.; Wu, Y.-K. Chin. J. Chem. 2004, 22, 999-1002.
39. (e) Suzuki, M.; Ohtake, H.; Kameya, Y.; Hamanaka, N.; Noyori, R. J. Org. Chem. 1989, 54, 5292-5302.
40. (f) Carman, R. M.; Rayner, A. C. Aust. J. Chem. 1994, 47, 195-202.
41. (g) Donkers, R. L.; Workentin, M. S. Chem. Eur. J. 2001, 7, 4012-4020.
42. 3 as the reductant, however, 3-4 h at the ambient temperature was required.
43. (a) Sanderson, J. R.; Paul, K.; Story, P. R.; Denson, D. D.; Alford, J. A. Synthesis 1975, 159-161.
44. (b) Xu, W.-L.; Chen, Y.-F.; Zhang, S.-L. Chem. Res. Chin. Univ. 1999, 15, 329-332.