Highly functionalised cyclobutanols via samarium(II) iodide-induced pinacol cyclisations of carbohydrate-derived 1,4-diketones

Carbohydrate Research

Volumn 340, Issue 7, 2005, Pages 1301-1309

  Williams, D Bradley G ^a   Caddy, Judy ^a   Blann, Kevin ^a  

^a UNIVERSITY OF JOHANNESBURG   (South Africa)

Author keywords

Carbocycles; Carbohydrates; Radical reactions; Samarium

Indexed keywords

CARBOHYDRATES; DERIVATIVES; KETONES; SYNTHESIS (CHEMICAL);

ANTI-VIRAL AGENTS; CYCLOBUTANEDIOL PRODUCTS; CYCLOBUTANOLS; MOIETIES;

SAMARIUM COMPOUNDS;

1 (1 BUTYL) 2 METHYL 3,4 O ISOPROPYLIDENE CYCLOBUTANE 1,2,3,4 TETRAOL; 1 (1 BUTYL) 5 O TERT BUTYLDIMETHYLSILYL 2,3 O ISOPROPYLIDENE RIBITOL; 1 O TERT BUTYLDIMETHYLSILYL 1,3,4 TRIHYDROXY 3,4 O ISOPROPYLIDENE 1 (THIOPHEN 2 YL) 2,5 PENTANEDIONE; 1 O TERT BUTYLDIMETHYLSILYL 1,3,4 TRIHYDROXY 3,4 O ISOPROPYLIDENE 2,5 NONANEDIONE; 1,3,4 TRIS(BENZYLOXY) 2,5 NONANEDIONE; 1,4 DIKETONE; 2 METHYL 1 PHENYL 3,4 O ISOPROPYLIDENE CYCLOBUTANE 1,2,3,4 TETRAOL; 2 METHYL 3,4 O ISOPROPYLIDENE 1 (THIOPHEN 2 YL)CYCLOBUTANE 1,2,3,4 TETRAOL; 2 TERT BUTYLDIMETHYLSILYLOXYMETHYL 3,4 O ISOPROPYLIDENE 1 (THIOPHEN 2 YL)CYCLOBUTANE 1,2,3,4 TETRAOL; 2,3 DIHYDROXY 2,3 O ISOPROPYLIDENE 1 (THIOPHEN 2 YL) 1,4 PENTANEDIONE; 2,3 DIHYDROXY 2,3 O ISOPROPYLIDENE 1 PHENYL 1,4 PENTANEDIONE; 2,3,5 TRI O BENZYL 1 (1 BUTYL)ARABINITOL; 2,3,5 TRI O BENZYL 1 (THIOPHEN 2 YL)ARABINITOL; 2,3,5 TRIS(BENZYLOXY) 1 (THIOPHEN 2 YL) 1,4 PENTANEDIONE; 3,4 DI O BENZYL 2 [(BENZYLOXY)METHYL] 1 (THIOPHEN 2 YL)CYCLOBUTANE 1,2,3,4 TETRAOL; 3,4 DI O BENZYL 2 [(BENZYLOXY)METHYL] 1 BUTYLCYCLOBUTANE 1,2,3,4 TETRAOL; 3,4 DIHYDROXY 3,4 O ISOPROPYLIDENE 2,5 NONANEDIONE; 5 O TERT BUTYLDIMETHYLSILYL 2,3 O ISOPROPYLIDENE 1 (THIOPHEN 2 YL)RIBITOL; 5 O TERT BUTYLDIMETHYLSILYL 2,3 O ISOPROPYLIDENE RIBOSE; ARABINOSE; BUTANOL; CARBOHYDRATE DERIVATIVE; CYCLOBUTANE DERIVATIVE; RIBOSE; SAMARIUM; SAMARIUM IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLIZATION; PINACOL REARRANGEMENT; PRIORITY JOURNAL;

EID: 18044376834     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2005.02.006     Document Type: Article

References (48)

1. R. Fittig Liebigs Ann. Chem. 110 1859 23 45
2. K.C. Nicolaou, Z. Yang, J.-J. Lui, P.G. Nantemet, C.F. Claiborne, J. Renaud, R.K. Guy, and K. Shibayama J. Am. Chem. Soc. 117 1995 645 652
3. J.L. Chiara, and N. Valle Tetrahedron: Asymmetry 6 1995 1895 1898
4. J.L. Chiara, and M. MartIÍn-Lomas Tetrahedron Lett. 35 1994 2969 2972
5. C. Anies, A. Pancrazi, J.-Y. Lallemand, and T. Prangè Tetrahedron Lett. 35 1994 7771 7774
6. For reviews, see: G.M. Robertson B.M. Trost Comprehensive Organic Synthesis Vol. 3 1990 Pergamon New York 563 611
7. J.E. McMurry Chem. Rev. 89 1989 1513 1524
8. B.E. Kahn, and R.D. Rieke Chem. Rev. 88 1988 733 745
9. J.L. Namy, J. Souppe, and H.B. Kagan Tetrahedron Lett. 24 1983 765 766
10. G.A. Molander, and C. Kenny J. Am. Chem. Soc. 111 1989 8236 8246
11. J.J.C. Grové, C.W. Holzapfel, and D.B.G. Williams Tetrahedron Lett. 37 1996 1305 1308
12. J.J.C. Grové, C.W. Holzapfel, and D.B.G. Williams Tetrahedron Lett. 37 1996 5817 5820
13. J.J.C. Grové, and C.W. Holzapfel Carbohydr. Lett. 2 1996 329 332
14. J.J.C. Grové, and C.W. Holzapfel Tetrahedron Lett. 38 1997 7429 7432
15. R.J. Ferrier, and S. Middleton Chem. Rev. 93 1993 2779 2831
16. T. Kan, S. Nara, T. Ozawa, H. Shirahama, and F. Matsuda Angew. Chem., Int. Ed. 39 2000 355 357 and references cited therein
17. J.L. Chiara, W. Cabri, and S. Hanessian Tetrahedron Lett. 32 1991 1125 1128
18. J. Uenishi, S. Masuda, and S. Wakabayashi Tetrahedron Lett. 32 1991 5097 5100
19. H.M.R. Hoffmann, A.M. El-Khawaga, and H.-H. Oehlerking Chem. Ber. 124 1991 2147
20. T. Maruyama, Y. Hanai, Y. Sato, R. Snoeck, G. Andrei, M. Hosoya, J. Balzarini, and E. De Clercq Chem. Pharm. Bull. 41 1993 516 519
21. B. Brown, and L.S. Hegedus J. Org. Chem. 63 1998 8012 8018
22. M. MartIÍn-Vilà, C. Minguillón, and R.M. Ortuño Tetrahedron: Asymmetry 9 1998 4291 4294
23. Godfrey, J. D. Jr.; Mueller, R. H. Bristol-Myers Squibb Co., US 5773614, 1998
24. Chem. Abstr. 129 1998 122668b
25. Kleeman, M.; Kahling, J.; Griss, G.; Hurnaus, R. Thomae, K, G.m.b.H., 1975, Ger. Offen. 2349639
26. Chem. Abstr. 83 1975 193390x
27. Kleeman, M.; Kahling, J.; Griss, G.; Hurnaus, R. Thomae, K, G.m.b.H., 1974, Ger. Offen. 2255439
28. Chem. Abstr. 81 1974 49702s
29. D.B.G. Williams, and K. Blann Eur. J. Org. Chem. 2004 3286 3291
30. Williams, D. B. G.; Blann, K.; Holzapfel, C. W. ZA 2002/2457, 2002
31. H.M.R. Hoffmann, I. Munnich, O. Nowitzki, H. Stucke, and D.J. Williams Tetrahedron 52 1996 11783 11798
32. O. Nowitzki, I. Münnich, H. Stucke, and H.M.R. Hoffmann Tetrahedron 52 1996 11799 11810
33. For a review on samarium-mediated fragmentation reactions, see: D.B.G. Williams, K. Blann, and J. Caddy Org. Prep. Proc. Int. 33 2001 565 602
34. D.B.G. Williams, J. Caddy, and K. Blann Org. Prep. Proc. Int. 35 2003 307 360
35. D. Horton, and A. Liav Carbohydr. Res. 47 1976 326 331
36. C.H. Shunk, J.B. Lavigne, and K. Folkers J. Am. Chem. Soc. 77 1955 2210 2212
37. G.M. Escandar, and L.F. Sala Org. Prep. Proced. Int. 22 1990 623 626
38. W.J. Evans, T.S. Gummersheimer, and J.W. Ziller J. Am. Chem. Soc. 117 1995 8999 9002 and references cited therein
39. F.A. Cotton, and G. Wilkinson Advanced Inorganic Chemistry 5th ed. 1988 John Wiley and Sons New York pp 959-961
40. M. Shabangi, and R.A. Flowers Jr. Tetrahedron Lett. 38 1997 1137 1140
41. J.-S. Shiue, C.-C. Lin, and J.-M. Fang Tetrahedron Lett. 34 1993 335 338
42. N. Kise, T. Suzumoto, and T. Sono J. Org. Chem. 59 1994 1407 1413
43. Blann, K. Ph.D. Thesis, Rand Afrikaans University, 2002
44. D.B.G. Williams, K. Blann, and C.W. Holzapfel J. Org. Chem. 65 2000 2834 2836
45. D.B.G. Williams, K. Blann, and C.W. Holzapfel Synth. Commun. 31 2001 203 209
46. D.B.G. Williams, K. Blann, and C.W. Holzapfel J. Chem. Soc., Perkin Trans. 1 2001 219 220
47. D.B.G. Williams, J. Caddy, K. Blann, and C.W. Holzapfel Synth. Commun. 32 2002 3755 3762
48. M. Yokoyama, T. Akiba, Y. Ochiai, A. Momotake, and H. Togo J. Org. Chem. 61 1996 6079 6092