Synthesis of stereodefined fused δ-hydroxy-γ-lactones from dealkylative cyclization of epoxy-diesters

Tetrahedron Letters

Volumn 52, Issue 37, 2011, Pages 4716-4719

  Pehlivan, Leyla ^a   Jacolot, Maïwenn ^a   Coia, Nicolas ^a   Monteiro, Nuno ^a   Bouyssi, Didier ^a   Balme, Genevive ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Cyclization; Diastereoselectivity; Epoxide; Fused hydroxy lactone

Indexed keywords

ALKENE; DELTAHYDROXY GAMMA LACTONE; EPOXIDE; EPOXYDIESTER; ESTER DERIVATIVE; GAMMA LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; DEALKYLATION; DRUG SYNTHESIS; EPOXIDATION; LACTONIZATION; STEREOCHEMISTRY;

EID: 80051693580     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.106     Document Type: Article

References (39)

1. X. Yang, and Y. Shimizu Tetrahedron Lett. 34 1993 761 764
2. G. Schlewer, J.-L. Stampf, and C. Benezra J. Med. Chem. 23 1980 1031 1038
3. M.-H. Xu, W. Wang, L.-J. Xia, and G.-Q. Lin J. Org. Chem. 66 2001 3953 3962
4. B.S. Davidson, and C.M. Ireland J. Nat. Prod. 53 1990 1036 1038
5. S. Hanessian, P.J. Murray, and S.P. Sahoo Tetrahedron Lett. 26 1985 5623 5626
6. S. Hanessian, P.J. Murray, and S.P. Sahoo Tetrahedron Lett. 26 1985 5627 5630
7. J.R. Wheatley, C.J.F. Bichard, S.J. Mantell, J.C. Son, D.J. Hughes, G.W.J. Fleet, and D.J. Brown Chem. Soc., Chem. Commun. 1993 1065 1067
8. M. Gasey, A.C. Manoge, and P.J. Murphy Tetrahedron Lett. 33 1992 965 968
9. L. Delhaye, A. Merschaert, K. Diker, and I.N. Houpis Synthesis 2006 1437 1443
10. For some recent reviews on the synthesis of γ-lactones see: S. Gil, M. Parra, P. Rodriguez, and J. Segura Mini-Rev. Org. Chem. 6 2009 345 358
11. M. Seitz, and O. Reiser Curr. Opin. Chem. Biol. 9 2005 285 292
12. D. Bouyssi, M. Cavicchioli, S. Large, N. Monteiro, and G. Balme Synlett 2000 749 751
13. K. Nacro, M. Baltas, J.-M. Escudier, and L. Gorrichon Tetrahedron 53 1997 659 672
14. M. Enomoto, and S. Kuwahara Angew. Chem., Int. Ed. 48 2009 1144 1148
15. K. Nacro, L. Gorrichon, J.-M. Escudier, and M. Baltas Eur. J. Org. Chem. 22 2001 4247 4258
16. R.M. Owen, and W.R. Roush Org Lett. 7 2005 3941 3944
17. S. Antoniotti, and E. Duñach Tetrahedron Lett. 50 2009 2536 2539
18. A.S. Kende, and B.H. Toder J. Org. Chem. 47 1982 163 167
19. P. Mohr, L. Rösslein, and C. Tamm Tetrahedron Lett. 30 1989 2513 2516
20. J.M. Concellon, E. Riego, and P.L. Bernad Org. Lett. 4 2002 1303 1305
21. J.-X. Wang, C.-X. Zhang, Y. Li, and Q.-D. You J. Chin. Chem. Soc. 53 2006 349 358
22. H. Urano, M. Enomoto, and S. Kuwahara Biosci. Biotechnol. Biochem. 74 2010 152 157
23. Radical cyclization: E. Baciocchi, A.B. Paolobelli, and R. Ruzziconi Tetrahedron 48 1992 4617 4622
24. L.H. Powel, P.H. Docherty, D.G. Hulcoop, P.D. Kemmitt, and J.W. Burton Chem. Commun. 2008 2559 2561
25. J.J. Davies, T.M. Krulle, and J.W. Burton Org. Lett 12 2010 2738 2741
26. Iodocyclization: D.P. Curran, and C.-T. Chang J. Org. Chem. 54 1989 3140 3157
27. O. Kitagawa, T. Inoue, K. Hirano, and T. Taguchi J. Org. Chem. 58 1993 3106 3112
28. T. Inoue, O. Kitagawa, Y. Oda, and T. Taguchi J. Org. Chem. 61 1996 8256 8263
29. All unsaturated substrates used in this study were obtained according to procedures previously reported by our group: for the preparation of stereodefined arylidene- and alkylidene-cyclopentanes 4a-d, 4h-j, and 4l, see: S. Montel, D. Bouyssi, and G. Balme Adv. Synth. Catal. 352 2010 2315 2320
30. For the synthesis of substituted methylenecyclopentanes 4e-g, see: N. Coia, D. Bouyssi, and G. Balme Eur. J. Org. Chem. 2007 3158 3165
31. For the synthesis of methylenecyclopentane 4m, see: D. Bouyssi, N. Monteiro, and G. Balme Tetrahedron Lett. 40 1999 1297 1300
32. For the synthesis of 4k see: G. Fournet, G. Balme, and J. Gore Tetrahedron 47 1991 6293 6304
33. K. Ishikawa, H.C. Charles, and G.W. Griffin Tetrahedron Lett. 1977 427 430
34. Crystallographic data for compound 5a have been deposited with the Cambridge Crystallographic Data Centre, No CCDC 819990. Copies of the data can be obtained, free of charge, on application to CCDC (e-mail: deposit@ccdc.cam.ac.uk).
35. The instability of such electron-rich aryl epoxides has previously been reported see: D.J. Aldous, A.S. Batsanov, D.S. Yufit, A.J. Dalenon, W.M. Dutton, and P.G. Steel Org. Biomol. Chem. 4 2006 2912 2927
36. C. Wawrzenczyk, M. Grabarczyk, A. Bialonska, and Z. Ciunik Tetrahedron 59 2003 6595 6601
37. A.W. Erian, S.M. Sherif, and H.M. Gaber Molecules 8 2003 793 865
38. G.A. Olah, M. Arvanaghi, and Y.D. Vankar J. Org. Chem. 45 1980 3531 3532
39. See Jacolot, M.; Pehlivan, L.; Bouyssi, D.; Monteiro, N.; Balme, G. next paper.