First organophosphorus radical-mediated cyclisations to afford medium-sized rings: Eight-membered lactones and seven- and eight-membered lactams

Tetrahedron Letters

Volumn 46, Issue 23, 2005, Pages 4027-4030

  Lang, Stuart ^a   Corr, Michael ^a   Muir, Neil ^a   Khan, Tanweer A ^a   Schönebeck, Franziska ^a   Murphy, John A ^a   Payne, Andrew H ^b   Williams, Andrew C ^c  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

Cyclisation; DEPO; EPHP; Phosphorus; Radical

Indexed keywords

LACTAM DERIVATIVE; LACTONE DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; PHOSPHINE DERIVATIVE; PHOSPHITE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 18844424348     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.032     Document Type: Article

References (57)

1. See: D.L.J. Clive, and J. Wang J. Org. Chem. 67 2002 1192 and extensive references therein
2. C. Chatgilialoglu, D. Griller, and M. Lesage J. Org. Chem. 53 1988 3641
3. K.J. Kulicke, and B. Giese Synlett 1990 91
4. C. Chatgilialoglu Acc. Chem. Res. 25 1992 188
5. C. Chatgilialoglu Organosilanes in Radical Chemistry 2003 Wiley
6. See, for example, H. Yorimitsu, and K. Oshima Radicals in Organic Synthesis 2000 Wiley-VCH pp 11-27
7. A.-P. Schaffner, and P. Renaud Eur. J. Org. Chem. 2004 2291 2298
8. S.Z. Zard Radicals in Organic Synthesis 2000 Wiley-VCH pp 90-108
9. D.O. Jang Tetrahedron Lett. 37 1996 5567
10. H. Yorimitsu, H. Shinokubo, and K. Oshima Bull. Chem. Soc. Jpn. 74 2001 225
11. S. Deprèle, and J.-L. Montchamp J. Org. Chem. 66 2001 6745
12. H. Yorimitsu, H. Shinokubo, and K. Oshima Synlett 2002 674
13. H. Nambu, A.H. Alinejad, K. Hata, H. Fujioka, and Y. Kita Tetrahedron Lett. 45 2004 8927
14. O. Dubert, A. Gautier, E. Condamine, and S.R. Piettre Org. Lett. 4 2002 359
15. D.H.R. Barton, D.O. Jang, and J.Cs. Jaszberenyi Tetrahedron Lett. 33 1992 5709
16. Calderon, J. M. B.; Chicharro, G. J.; Fiandhorn, R. J.; Huss, S.; Ward, R. A.; EP 2284 970506, 1997
17. R. McCague, R.G. Pritchard, R.J. Stoodley, and D.S. Williamson Chem. Commun. 1998 2691
18. S.R. Graham, J.A. Murphy, and D. Coates Tetrahedron Lett. 40 1999 2415
19. S.R. Graham, J.A. Murphy, and A.R. Kennedy J. Chem. Soc., Perkin Trans. 1 1999 3071
20. Y. Kita, H. Nambu, N.G. Ramesh, G. Anilkumar, and M. Matsugi Org. Lett. 3 2001 1157
21. S.C. Roy, C. Guin, K.K. Kumar, and G. Maiti Tetrahedron 58 2002 2435
22. D.O. Jang, and D.H. Cho Tetrahedron Lett. 43 2002 5921
23. D.W. Thomson, A.G.J. Commeureuc, S. Berlin, and J.A. Murphy Synth. Commun. 33 2003 3631
24. S. Caddick, D. Hamza, D.B. Judd, M.T. Reich, S.N. Wadman, and J.D. Wilden Tetrahedron Lett. 45 2004 2363
25. D.Y. Cho, and D.O. Jang Synlett 2005 59 For fuller list of references, see Ref. 9
26. J.M. Barks, B.C. Gilbert, A.F. Parsons, and B. Upeandran Tetrahedron Lett. 42 2001 3137
27. J.M. Barks, B.C. Gilbert, A.F. Parsons, and B. Upeandran Synlett 2001 1719
28. C.M. Jessop, A.F. Parsons, A. Routledge, and D. Irvine Tetrahedron Lett. 44 2003 479
29. C.M. Jessop, A.F. Parsons, A. Routledge, and D.J. Irvine Tetrahedron: Asymmetry 14 2003 2849
30. C.M. Jessop, A.F. Parsons, A. Routledge, and D.J. Irvine Tetrahedron Lett. 45 2004 5095
31. T.A. Khan, R. Tripoli, J.J. Crawford, C.G. Martin, and J.A. Murphy Org. Lett. 5 2003 2971
32. T. Laird, S.A. Hermitage, and U. Tilstam Org. Process Res. Dev. 7 2003 776
33. See however Ref. 15c, which suggests that this is unlikely for the ester substrates
34. 3 solution (100 mL), 1 M HCl (100 mL) and washed with brine (100 mL). The organic layer was dried, filtered and the solvent removed and purified by column chromatography (silica: 5-10% EtOAc in heptane) to afford the desired lactone/lactam
35. 2O (30 mL). The organic layer was dried, filtered and concentrated in vacuo. The mixture was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (90/10-85/15) to afford the desired lactone/lactam
36. G.E. Keck, and D.A. Burnett J. Org. Chem. 52 1987 2958
37. H. Yorimitsu, K. Wakabayashi, H. Shinukobo, and K. Oshima Tetrahedron Lett. 40 1999 519
38. For examples of radical-based preparation of eight-membered rings, see B.B. Snider, and J.E. Merritt Tetrahedron 47 1991 8663
39. T. Sato, S. Ishida, H. Ishibashi, and M. Ikeda J. Chem. Soc., Perkin Trans. 1 1991 353
40. E. Lee, C.H. Yoon, and T.H. Lee J. Am. Chem. Soc. 114 1992 10981
41. G.A. Molander, and J.A. McKie J. Org. Chem. 59 1994 3186
42. K. Ghosh, A.K. Ghosh, and U.R. Ghatak J. Chem. Soc., Chem. Commun. 1994 629
43. E. Lee, and C.H. Yoon Tetrahedron Lett. 37 1996 5929
44. G.A. Russell, and C. Li Tetrahedron Lett. 37 1996 2557
45. P. Chattopadhyay, M. Mukherjee, and S. Ghosh J. Chem. Soc., Chem. Commun. 1997 2139
46. E. Lee, C.H. Yoon, T.H. Lee, S.Y. Kim, T.J. Ha, Y. Sung, S.-H. Park, and S. Lee J. Am. Chem. Soc. 120 1998 7469
47. L. Manzoni, L. Belvisi, and C. Scolastico Synlett 2000 1287
48. L.G. Monovich, Y. Le Huérou, M. Rönn, and G.A. Molander J. Am. Chem. Soc. 122 2000 52
49. J. Marco-Contelles, and E. de Opazo Tetrahedron Lett. 41 2000 5341
50. A. Nandi, and P. Chattopadhyay Tetrahedron Lett. 43 2002 5977
51. G.A. Molander, K.M. George, and L.G. Monovich J. Org. Chem. 68 2003 9533
52. Typical DEPO in water experimental procedure: Water (3-4 mL) was boiled for 10 min under nitrogen and then the substrate [1 equiv (0.04-0.86 mmol)] and DEPO (10 equiv) were added. VA-501 (0.5 equiv) was added after 5 min and mixture was heated for 6 h at 80°C. VA-501 (0.5 equiv) was added again and mixture was further heated for 6 h. The mixture was cooled and sodium hydroxide (2 N, 15 mL) was added and then finally the mixture was extracted with diethyl ether (20 mL × 3). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The mixture was purified by column chromatography on silica gel using petroleum ether/EtOAc (90/10-85/15) to afford the desired lactam
53. M. Kosugi, Y. Shimizu, and T. Migita Chem. Lett. 1977 1423
54. J.K. Stille Angew. Chem., Int. Ed. Engl. 25 1986 508
55. A.L.J. Beckwith, and J.M.D. Storey J. Chem. Soc., Chem. Commun. 1995 977
56. D.P. Curran, H.S. Yu, and H.T. Liu Tetrahedron 50 1994 7343 and references cited therein
57. Semi-empirical (AM1) calculations were performed using Spartan'04 for Windows provided by Wavefunction Inc