Highly Functionalized Cyclopentanes by Radical Cyclization of Unsaturated Bromolactones. 2. A Facile Synthesis of the First Carbaaldohexofuranoses and Their Conversion to Carbapentofuranoses

Journal of Organic Chemistry

Volumn 63, Issue 6, 1998, Pages 1919-1928

  Horneman, Anne Marie ^a   Lundt, Inge ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

5 AMINO 5 DEOXYCARBA GLUCOFURANOSE; 7 BROMO 7 DEOXY HEPTONO 1,4 LACTONE; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; CARBA GLUCOFURANOSE; CARBA LYXOFURANOSE; CARBA MANNOFURANOSE; CARBA PENTOFURANOSE; CARBA XYLOFURANOSE; CYCLOPENTANE DERIVATIVE; LACTONE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032549580     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971928l     Document Type: Article

References (46)

1. Nishimura, Y. In Studies in Natural Products Chemistry; Attaur-Rahman, Ed.; Elsevier Publishers B. V.: Amsterdam, 1992; Vol. 10, p 495.
2. Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571.
3. Agrofolio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
4. Trost, B. M.; Madsen, R.; Guile, S. G.; Elia, A. E. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1569.
5. King, S. B.; Ganem, B.; J. Am. Chem. Soc. 1994, 116, 562.
6. Trost, B. M.; van Vranken, D. L. J. Am. Chem. Soc., 1993, 115, 444.
7. Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779.
8. Vogel, P.; Fattori, D.; Gasparoni, F.; Le Drian, C. Synlett 1990, 173.
9. Marschner, C.; Penn, G.; Griengl, H. Tetrahedron Lett. 1990, 31, 2873. Idem. Tetrahedron 1993, 49, 5067.
10. Marschner, C.; Penn, G.; Griengl, H. Tetrahedron Lett. 1990, 31, 2873. Idem. Tetrahedron 1993, 49, 5067.
11. (a) Shoberu, K. A.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1992, 2419.
12. (b) Parry, R. J.; Haridas, K.; De Jong, R.; Johnson, C. R. Tetrahedron Lett., 1990, 31, 7549.
13. (a) Mother-well, W. B.; Crich, D.; Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992.
14. (b) Giese, B. Radicals in Organic Synthesis, Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986.
15. (a) Wilcox, C. S.; Thomasco, L. M. J. Org. Chem. 1985, 50, 546.
16. (b) Gaudino, J. J.; Wilcox, C. S. Carbohydr. Res. 1990, 206, 233,
17. (a) Horneman, A. M.; Lundt, I.; Soetofte, I. Synlett 1995, 918.
18. (b) Horneman, A. M.; Lundt, I. Tetrahedron 1997, 53, 6879.
19. Suami, T.; Ogawa, S. Adv. Carbohydr. Chem. Biochem. 1990, 48, 21.
20. Marschner, C.; Baumgartner, J.; Griengl, H. J. Org. Chem. 1995, 60, 5224.
21. Roberts, S. M.; Shoberu, K. A. J. Chem. Soc., Perkin Trans, 1 1992, 2625.
22. Lundt, I.; Madsen, R.; Synthesis, 1995, 787.
23. Lederkremer, R. M. de; Varela, O. Adv. Carbohydr. Chem. Biochem. 1994, 50, 125.
24. (a) Vekemans, J. A. J. M.; Dapperens, G. W. M.; Ciaessen, R.; Kten, A. M. J.; Godefrei, E. F.; Chittenden, G. J. F. J. Org. Chem. 1990, 55, 5336.
25. (b) Vekemans, J. A. J. M.; De Bruyn, R. G. M.; Caris, R. C. H. M.; Kokx, A. J. P. M.; Konings, J. J. H. G.; Godefrei, E. F.; Chittenden, G. J. F. J. Org. Chem. 1987, 52, 1093.
26. (c) Vekemans, J. A. J. M.; Franken, G. A. M.; Dapperens, C. W. M.; Godefrei, E. F.; Chittenden, G. J. F. J. Org. Chem. 1988, 53, 627.
27. 32 established the configuration at C-4 of 7 and 10.
28. Giese, B. Org. React. 1996, 48, 301.
29. Tadano, K.; Hoshino, H.; Ogawa, S.; Suami, T. J. Org. Chem. 1988, 53, 1427.
30. Bock, K.; Lundt, I.; Pedersen, C. Acta Chem. Scand. 1987,B41, 435. Bols, M.; Lundt, I. Ibid. 1988, B42, 67.
31. Bock, K.; Lundt, I.; Pedersen, C. Acta Chem. Scand. 1987,B41, 435. Bols, M.; Lundt, I. Ibid. 1988, B42, 67.
32. Wassermann, H. H.; Brunner, R. K.; Buynak, J. D.; Carter, C. G.; Oku, T.; Robinson, R. P. J. Am. Chem. Soc., 1985, 107, 519.
33. Knouzi, N.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr. 1985, 815.
34. (a) Obata, N.; Niimura, K. J. Chem. Soc., Chem. Commun. 1977, 238.
35. (b) For reviews on amino acid derived radicals see Easton, C. J. Chem. Rev. 1997, 97, 53.
36. (c) Renaud, P.; Giraud, L. Synthesis 1996, 913.
37. Aggarwal, V. K.; Monteiro, N.; Tarver, G. J.; Lindeil, S. D. J. Org. Chem. 1996, 61, 1192.
38. Varela, O.; Nin, A. P.; Lederkremer, R. M. de. Tetrahedron Lett. 1994, 35, 9359.
39. (a) Stork, G.; Sher, P. M.; Chen, H. L. J. Am. Chem. Soc. 1986, 108, 6384.
40. (b) Keck, G. E.; Bumett, D. A. J. Org. Chem. 1987, 52, 2958.
41. (c) Renaud, P.; Schubert, S. Angew. Chem. 1990, 102, 416.
42. (d) For a general treatment of stereoselectivity in radical reactions see Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; Verlag Chemie: New York, 1996.
43. Hayashi, K.; lyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81.
44. (a) Bock, K.; Lundt, I.; Pedersen, C. Acta Chem. Scand. 1981, B35, 155.
45. (b) Hussain, S. A. M. T.; Ollis, W. D.; Smith, C.; Stoddart, J. F. J. Chem. Soc., Perkin Trans. 1 1975, 1480.
46. Bock, K.; Lundt, I.; Pedersen, C.; Sonnichsen, R. Carbohydr. Res. 1988, 174, 331.