Synthesis and photoinitiated radical cyclization of allyl- and propynyloxymethyl substituted cyclopentanones to tetrahydrocyclopenta[c]furanols

Tetrahedron Letters

Volumn 46, Issue 45, 2005, Pages 7751-7755

  Tzvetkov, Nikolay T ^a   Mattay, Jochen ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

Cyclopentafuranols; Cyclopentanones; H abstraction; Photochemistry; Radical cyclization

Indexed keywords

ACETONITRILE; BENZENE; CYCLOPENTANE DERIVATIVE; CYCLOPENTANONE DERIVATIVE; FURAN DERIVATIVE; SOLVENT;

ARTICLE; CYCLIZATION; ELECTRON TRANSPORT; IRRADIATION; LIGHT; SYNTHESIS;

EID: 26444488153     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.040     Document Type: Article

References (54)

1. J. Velcicky, J. Lex, and H.-G. Schmalz Org. Lett. 4 2002 565 568
2. J. Velcicky, A. Lanver, J. Lex, A. Prokop, T. Wieder, and H.-G. Schmalz Chem. Eur. J. 10 2004 5087 5110
3. L.A. Paquette Top. Curr. Chem. 119 1984 1 163
4. L.A. Paquette, and A.M. Doherty Polyquinane Chemistry 1987 Springer Berlin, Heidelberg
5. M.J. Begley, M. Ladlow, and G. Pattenden J. Chem. Soc., Perkin Trans. 1 1998 1095 1106
6. M. Ladlow, and G. Pattenden J. Chem. Soc., Perkin Trans. 1 1988 1107 1118
7. K.E.B. Parkes, and G. Pattenden J. Chem. Soc., Perkin Trans. 1 1988 1119 1134
8. C. Mehta, and A. Srikrishna Chem. Rev. 97 1997 671 719
9. D.P. Curran Synthesis 1988 417 439 and 489-513
10. D.P. Curran Synlett 1991 63 72
11. B. Giese Angew. Chem. 97 1985 555 566
12. B. Giese Angew. Chem., Int. Ed. Engl. 24 1985 553 565
13. B. Giese Radicals in Organic Synthesis: Formation of Carbon-Carbon Bond 1986 Pergamon Press Oxford
14. J. Cossy, and C. Leblanc Tetrahedron Lett. 30 1989 4531 4534
15. G. Pattenden, J.M. Clough, and P.G. Wight Tetrahedron Lett. 30 1989 7469 7472
16. C.-K. Sha, T.-S. Jean, and D.-C. Wang Tetrahedron Lett. 31 1990 3745 3748
17. N. Tzvetkov, M. Schmidtmann, A. Müller, and J. Mattay Tetrahedron Lett. 44 2003 5979 5982
18. J.E. Baldwin J. Chem. Soc., Chem. Commun. 1976 734 736
19. A.L.J. Beckwith Tetrahedron 37 1981 3073 3100
20. A.L.J. Beckwith, and C.H. Schiesser Tetrahedron 41 1985 3925 3941
21. J.M. Surzur R.A. Abramovitch Reactive Intermediates Vol. 2 1983 Plenum New York 164
22. T. Shono, I. Nishigushi, and H. Ohmizu Chem. Lett. 1976 1233 1236
23. G. Pattenden, and G.M. Robertson Tetrahedron Lett. 24 1983 4617 4620
24. G. Pattenden, and G.M. Robertson Tetrahedron 41 1985 4001 4011
25. R.D. Little, D.P. Fox, L.V. Hijfte, R. Dannecker, G. Sowell, R.L. Wolin, L. Moëns, and M.M. Baizer J. Org. Chem. 53 1988 2287 2294
26. T. Shono, and N. Kise Tetrahedron Lett. 31 1990 1303 1306
27. S. Hintz, A. Heidbreder, and J. Mattay Top. Curr. Chem. 177 1996 77 124
28. S.K. Pradhan, T.V. Radhakrishnan, and R. Subramanian J. Org. Chem. 41 1976 1943 1952
29. S.K. Pradhan, S.R. Kadam, J.N. Kolhe, T.V. Radhakrishnan, S.V. Sohani, and V.B. Thaker J. Org. Chem. 46 1981 2622 2633
30. S.K. Pradhan, S.R. Kadam, and J.N. Kolhe J. Org. Chem. 46 1981 2633 2638
31. G.A. Molander, and C.R. Harris Tetrahedron 54 1998 3321 3354
32. K. Kakiuchi, Y. Fujioka, H. Yamamura, K. Tsutsumi, T. Morimoto, and H. Kurosowa Tetrahedron Lett. 42 2001 7595 7598
33. P. Dowd, and W. Zhang Chem. Rev. 93 1993 2091 2115
34. D. Belotti, J. Cossy, J.-P. Pete, and C. Portella Tetrahedron Lett. 26 1985 4591 4594
35. D. Belotti, J. Cossy, J.-P. Pete, and C. Portella J. Org. Chem. 51 1986 4196 4200
36. J. Cossy Bull. Soc. Chim. Fr. 131 1994 344 356
37. J. Cossy, D. Belotti, and J.-P. Pete Tetrahedron 46 1990 1859 1870
38. J. Cossy, and C. Leblanc Tetrahedron Lett. 32 1991 3051 3052
39. J. Cossy, D. Belotti, and C. Leblanc J. Org. Chem. 58 1993 2351 2354
40. J. Cossy, D. Belotti, N.K. Cuong, and C. Chassagnard Tetrahedron 49 1993 7691 7700
41. J. Cossy, A. Madaci, and J.-P. Pete Tetrahedron Lett. 35 1994 1541 1544
42. Tzvetkov, N. T. Preliminary report: Ph.D. Dissertation, University of Bielefeld, 2005.
43. W. Horspool F. Lenci Organic Photochemistry and Photobiology 2nd ed. 2004 CRC Press New York Chapters 52, 57, and 58
44. Ethyl 2-oxocyclopentanecarboxylate 1 is commercially available (Fluka Ltd) or can be synthesized following known three-step procedure, see also J.P. Schäfer, and J.J. Bloomfield Org. React. 15 1967 1
45. K. Sisido, K. Utimoto, and T. Isida J. Am. Chem. Soc. 29 1964 2781 2782
46. P. Kumar, and K. Saravanan Tetrahedron 54 1998 2161 2168
47. D. Daniel, R. Middleton, H.L. Henry, and W.H. Okamura J. Org. Chem. 61 1996 5617 5625
48. D.F. Harvey, K.P. Lund, and D.A. Neil J. Am. Chem. Soc. 114 1992 8424 8434
49. Photochemical reactions were performed in a Rayonet RPR-100 photochemical chamber reactor (Southern New England Ultraviolet Company, Brandford) fitted with 16 lamps RPR-3000 Å (emission maximum at 300 nm half band width, each lamp 21 W) and merry-go-round inset using duran tubes (12 mL vol, 1 cm diameter). Deoxygenated with argon solutions (0.12 M) of the respective propynyl- and allyloxymethyl cyclopentanones, 5 and 7, were dissolved in dry benzene or acetonitrile and irradiated. The conversion of the starting material was monitored by GC and/or GC-MS.
50. M.B. Smith, and J. March March's Advanced Organic Chemistry 2001 John Wiley & Sons New York Chapter 7
51. D.I. Schuster Patai Rappoport The Chemistry of Enones 1989 John Wiley & Sons New York 623 Part 2
52. The calculations were carried out using Titan V1.05, Schrödinger Inc., Wavefunction Inc., 2000.
53. G. Büchi, C.G. Inman, and E.S. Lipinsky J. Am. Chem. Soc. 76 1954 4327 4331
54. I. Nonomija, and T. Naito Photochemical Synthesis 1989 Academic Press New York pp 138-151