Synthesis of chiral, densely functionalized medium-sized rings from carbohydrate precursors via regioselective exo/endo-primary alkyl radical cyclizations

Tetrahedron Letters

Volumn 41, Issue 28, 2000, Pages 5341-5345

  Marco Contelles, José ^a   de Opazo, Elsa ^a  

^a CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; CARBOHYDRATE; FREE RADICAL; GLUCOSE;

ACETYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONFORMATION; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034622395     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00837-6     Document Type: Article

References (45)

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26. For some examples of 7-exo cyclizations, see: (a) Clark, A. J.; Jones, K.; McCarthy, C.; Storey, J. M. D. Tetrahedron Lett. 1991, 32, 2829; (b) Booth, S. E.; Jenkins, P. R.; Swain, C. J. J. Chem. Soc., Chem. Commun. 1991, 1248; (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429; (d) Kim, S.; Kee, I. S. Tetrahedron Lett. 1993, 34, 4213; (e) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051; (f) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Synlett 1997, 580; (g) Yuasa, Y.; Sato, W. Shibuya, S. Synth. Commun. 1997, 27, 573; (h) Evans, P. A.; Manangan, T. Tetrahedron Lett. 1997, 38, 8165.
27. For some examples of 7-exo cyclizations, see: (a) Clark, A. J.; Jones, K.; McCarthy, C.; Storey, J. M. D. Tetrahedron Lett. 1991, 32, 2829; (b) Booth, S. E.; Jenkins, P. R.; Swain, C. J. J. Chem. Soc., Chem. Commun. 1991, 1248; (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429; (d) Kim, S.; Kee, I. S. Tetrahedron Lett. 1993, 34, 4213; (e) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051; (f) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Synlett 1997, 580; (g) Yuasa, Y.; Sato, W. Shibuya, S. Synth. Commun. 1997, 27, 573; (h) Evans, P. A.; Manangan, T. Tetrahedron Lett. 1997, 38, 8165.
28. For some examples of 7-exo cyclizations, see: (a) Clark, A. J.; Jones, K.; McCarthy, C.; Storey, J. M. D. Tetrahedron Lett. 1991, 32, 2829; (b) Booth, S. E.; Jenkins, P. R.; Swain, C. J. J. Chem. Soc., Chem. Commun. 1991, 1248; (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429; (d) Kim, S.; Kee, I. S. Tetrahedron Lett. 1993, 34, 4213; (e) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051; (f) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Synlett 1997, 580; (g) Yuasa, Y.; Sato, W. Shibuya, S. Synth. Commun. 1997, 27, 573; (h) Evans, P. A.; Manangan, T. Tetrahedron Lett. 1997, 38, 8165.
29. For some examples of 7-exo cyclizations, see: (a) Clark, A. J.; Jones, K.; McCarthy, C.; Storey, J. M. D. Tetrahedron Lett. 1991, 32, 2829; (b) Booth, S. E.; Jenkins, P. R.; Swain, C. J. J. Chem. Soc., Chem. Commun. 1991, 1248; (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429; (d) Kim, S.; Kee, I. S. Tetrahedron Lett. 1993, 34, 4213; (e) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051; (f) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Synlett 1997, 580; (g) Yuasa, Y.; Sato, W. Shibuya, S. Synth. Commun. 1997, 27, 573; (h) Evans, P. A.; Manangan, T. Tetrahedron Lett. 1997, 38, 8165.
30. For some examples of 7-exo cyclizations, see: (a) Clark, A. J.; Jones, K.; McCarthy, C.; Storey, J. M. D. Tetrahedron Lett. 1991, 32, 2829; (b) Booth, S. E.; Jenkins, P. R.; Swain, C. J. J. Chem. Soc., Chem. Commun. 1991, 1248; (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429; (d) Kim, S.; Kee, I. S. Tetrahedron Lett. 1993, 34, 4213; (e) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051; (f) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Synlett 1997, 580; (g) Yuasa, Y.; Sato, W. Shibuya, S. Synth. Commun. 1997, 27, 573; (h) Evans, P. A.; Manangan, T. Tetrahedron Lett. 1997, 38, 8165.
31. For some examples of 7-exo cyclizations, see: (a) Clark, A. J.; Jones, K.; McCarthy, C.; Storey, J. M. D. Tetrahedron Lett. 1991, 32, 2829; (b) Booth, S. E.; Jenkins, P. R.; Swain, C. J. J. Chem. Soc., Chem. Commun. 1991, 1248; (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429; (d) Kim, S.; Kee, I. S. Tetrahedron Lett. 1993, 34, 4213; (e) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051; (f) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Synlett 1997, 580; (g) Yuasa, Y.; Sato, W. Shibuya, S. Synth. Commun. 1997, 27, 573; (h) Evans, P. A.; Manangan, T. Tetrahedron Lett. 1997, 38, 8165.
32. For some examples of 7-exo cyclizations, see: (a) Clark, A. J.; Jones, K.; McCarthy, C.; Storey, J. M. D. Tetrahedron Lett. 1991, 32, 2829; (b) Booth, S. E.; Jenkins, P. R.; Swain, C. J. J. Chem. Soc., Chem. Commun. 1991, 1248; (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429; (d) Kim, S.; Kee, I. S. Tetrahedron Lett. 1993, 34, 4213; (e) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051; (f) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Synlett 1997, 580; (g) Yuasa, Y.; Sato, W. Shibuya, S. Synth. Commun. 1997, 27, 573; (h) Evans, P. A.; Manangan, T. Tetrahedron Lett. 1997, 38, 8165.
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37. Nitrone route: (a) Marco-Contelles, J.; de Opazo, E. Tetrahedron Lett. 1999, 40, 4445. Metathesis via: (b) Marco-Contelles, J.; de Opazo, E. Tetrahedron Lett., 2000, 41, 2439; (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem., in press.
38. Nitrone route: (a) Marco-Contelles, J.; de Opazo, E. Tetrahedron Lett. 1999, 40, 4445. Metathesis via: (b) Marco-Contelles, J.; de Opazo, E. Tetrahedron Lett., 2000, 41, 2439; (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem., in press.
39. Nitrone route: (a) Marco-Contelles, J.; de Opazo, E. Tetrahedron Lett. 1999, 40, 4445. Metathesis via: (b) Marco-Contelles, J.; de Opazo, E. Tetrahedron Lett., 2000, 41, 2439; (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem., in press.
40. (a) For an unique 7-endo-trig ring closure in a sugar derivative, see: Redlich, H.; Sudau, W.; Szardenings, A. K.; Vollerthum, R. Carbohydr. Res. 1992, 226, 57;
41. (b) For the 7-exo-dig free radical cyclization of a C-glycosyl radical onto a O-propargyl moiety, see: Kim, G., Kim, H. S. Tetrahedron Lett. 2000, 41, 225.
42. All new compounds showed good analytical and spectroscopic data. The synthesis of radical precursors 1-6 (from D-mannose) and 7, 11, 13 and 14 (from D-glucose) will be described elsewhere.
43. 5), 111.9, 109.9, 86.4, 80.0, 78.1, 74.9, 28.4, 26.9 (2×C), 25.9 (2×C).
44. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
45. Values in parenthesis refer to yields taking into account the recovered starting material.