Synthesis of disubstituted 1,2-dioxolanes, 1,2-dioxanes, and 1,2-dioxepanes

Tetrahedron

Volumn 66, Issue 1, 2010, Pages 157-163

  Guerra, Francisco M ^a   Zubía, Eva ^a   Ortega, María J ^a   Moreno Dorado, F Javier ^a   Massanet, Guillermo M ^a  

^a UNIVERSITY OF CÁDIZ   (Spain)

Author keywords

Bioactivity; Cyclic peroxides; Hydroperoxide cyclization; Stolonoxides

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; DIOXANE DERIVATIVE; ESTER DERIVATIVE; OXEPANE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLIZATION; MICHAEL ADDITION; NONHUMAN; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS;

MAMMALIA; STOLONICA SOCIALIS;

EID: 70749084728     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.11.026     Document Type: Article

References (41)

1. Fontana A., González M.C., Gavagnin M., Templado J., and Cimino G. Tetrahedron Lett. 41 (2000) 429-432
2. Durán R., Zubía E., Ortega M.J., Naranjo S., and Salvá J. Tetrahedron 56 (2000) 6031-6037
3. Durán, R.; Zubía, E.; Ortega, M. J.; Naranjo, S.; Salvá, J.; Fernández Puentes, J. L.; García Grávalos, M. D. PCT WO 01/83477 A1.
4. Davies-Coleman M.T., Cantrell C.L., Gustafson K.R., Beutler J.A., Pannell L.K., and Boyd M.R. J. Nat. Prod. 63 (2000) 1411-1413
5. Fontana A., Cimino G., Gavagnin M., González M.C., and Estornell E. J. Med. Chem. 44 (2001) 2362-2365
6. Nagle D.G., Zhou Y.-D., Mora F.D., Mohammed K.A., and Kim Y.-P. Curr. Med. Chem. 11 (2004) 1725-1756
7. Fujita D., Ichimaru N., Abe M., Murai M., Hamada T., Nishioka T., and Miyoshi H. Tetrahedron Lett. 46 (2005) 5775-5779
8. Zeng B.-B., Wu Y., Jiang S., Yu Q., Yao Z.-J., Liu V., Li H.-Y., Li Y., Chen X.-G., and Wu Y.-L. Chem.-Eur. J. 9 (2003) 282-290
9. Pinacho Crisóstomo F.R., Carrillo R., León L.G., Martín T., Padrón J.M., and Martín V.S. J. Org. Chem. 71 (2006) 2339-2345
10. Zmitek K., Zupan M., and Iskra J. Org. Biomol. Chem. 5 (2007) 3895-3908
11. Korshin E.E., and Bachi M.D. In: Rappoport Z. (Ed). Chemistry of Peroxides Vol. 2 (2006), John Wiley & Sons, Chichester 189-305
12. McCullough K.J., and Nojima M. Curr. Org. Chem. 5 (2001) 601-636
13. Bartlett P.A., and Chapuis C. J. Org. Chem. 51 (1986) 2799-2806
14. Murakami N., Kawanishi M., Itagaki S., Horii T., and Kobayashi M. Tetrahedron Lett. 42 (2001) 7281-7285
15. Murakami N., Kawanishi M., Itagaki S., Horii T., and Kobayashi M. Bioorg. Med. Chem. Lett. 12 (2002) 69-72
16. Murakami N., Kawanishi M., Itagaki S., Horii T., and Kobayashi M. Bioorg. Med. Chem. Lett. 14 (2004) 3513-3516
17. Kawanishi M., Kotoku N., Itagaki S., Horii T., and Kobayashi M. Bioorg. Med. Chem. Lett. 14 (2004) 5297-5307
18. Xu C., Raible J.M., and Dussault P.H. Org. Lett. 7 (2005) 2509-2511
19. Liu H.-H., Jin H.-X., Zhang Q., Wu Y.-K., Kim H.-S., and Wataya Y. Chin. J. Chem. 23 (2005) 1469-1473
20. Liu H.-H., Zhang Q., Jin H.-X., Shen X., and Wu Y.-K. Chin. J. Chem. 24 (2006) 1180-1189
21. Liu H.-H., Jin H.-X., and Wu Y.-K. Chin. J. Chem. 22 (2004) 1029-1033
22. Jin H.-X., Zhang Q., Kim H.-S., Wataya Y., Liu H.-H., and Wu Y. Tetrahedron 62 (2006) 7699-7711
23. O'Neill P.M., Searle N.L., Raynes K.J., Maggs J.L., Ward S.A., Storr R.C., Park B.K., and Posner G.H. Tetrahedron Lett. 39 (1998) 6065-6068
24. Harris J.R., Waetzig S.R., and Woerpel K.A. Org. Lett. 11 (2009) 3290-3293
25. Yu C., Liu B., and Hu L. Tetrahedron Lett. 41 (2000) 4281-4285
26. 2. Removal of the solvent in vacuo and replacement with the desired reaction solvent affords easily handled solution of the reagent. See:
27. Dussault P., and Sahli A. J. Org. Chem. 57 (1992) 1009-1012
28. Dussault P.H., Zope U.R., and Westermeyer T.A. J. Org. Chem. 59 (1994) 8267-8268
29. Dussault P. Synlett (1995) 997-1003
30. For 15a:. Ferrié L., Boulard L., Pradaux F., Bouzbouz S., Reymond S., Capdevielle P., and Cossy J. J. Org. Chem. 73 (2008) 1864-1880
31. For 15b:. Nonaka H., Maeda N., and Kobayashi Y. Tetrahedron Lett. 48 (2007) 5601-5604
32. For 15c:. Ferrié L., Reymond S., Capdevielle P., and Cossy J. Org. Lett. 8 (2006) 3441-3443
33. 2 in sulfuric acid:. Davies A.G., and Feld R. J. Chem. Soc. (1956) 665-670
34. However, the lability of the furan ring to these conditions led us to change the procedure:. Massa A., Palombi L., and Scettri A. Tetrahedron Lett. 42 (2001) 4577-4579
35. Dussault P., and Sahli A. Tetrahedron Lett. 31 (1990) 5117-5120
36. Zhang W., and Robins M.J. Tetrahedron Lett. 33 (1992) 1177-1180
37. Different silyl ether based protective groups were also tried but they were not robust enough to resist the hydroperoxide formation step.
38. Adam W., Rao P.B., Degen H.-G., and Saha-Moeller C.R. J. Am. Chem. Soc. 122 (2000) 5654-5655
39. Kornblum N., and De La Mare H.E. J. Am. Chem. Soc. 73 (1951) 880-881
40. The relative configuration of cis- and trans-diastereoisomers 5 were established by a study of NOESY-1D experiments.
41. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107-1112