Cycloheptenols from carbohydrates

Tetrahedron Letters

Volumn 41, Issue 14, 2000, Pages 2439-2441

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

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CARBOHYDRATE DERIVATIVE; CYCLOALKANE DERIVATIVE; CYCLOHEPTENOL; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0034175668     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00150-7     Document Type: Article

References (40)

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16. For a review and some references, see: (a) Molander, G. A. Acc. Chem. Res. 1998, 31, 603. (b) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940, and Ref. 3 cited therein. (c) Molander, G. A.; Sono, M. Tetrahedron Lett. 1998, 54, 9289. (d) Malpass, J. R.; Wallis, A. L. Tetrahedron 1998, 54, 3631. (e) Pearson, A. J.; Srinivasan, K. J. Org. Chem. 1992, 57, 3965.
17. For a review and some references, see: (a) Molander, G. A. Acc. Chem. Res. 1998, 31, 603. (b) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940, and Ref. 3 cited therein. (c) Molander, G. A.; Sono, M. Tetrahedron Lett. 1998, 54, 9289. (d) Malpass, J. R.; Wallis, A. L. Tetrahedron 1998, 54, 3631. (e) Pearson, A. J.; Srinivasan, K. J. Org. Chem. 1992, 57, 3965.
18. For a review and some references, see: (a) Molander, G. A. Acc. Chem. Res. 1998, 31, 603. (b) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940, and Ref. 3 cited therein. (c) Molander, G. A.; Sono, M. Tetrahedron Lett. 1998, 54, 9289. (d) Malpass, J. R.; Wallis, A. L. Tetrahedron 1998, 54, 3631. (e) Pearson, A. J.; Srinivasan, K. J. Org. Chem. 1992, 57, 3965.
19. For a review and some references, see: (a) Molander, G. A. Acc. Chem. Res. 1998, 31, 603. (b) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940, and Ref. 3 cited therein. (c) Molander, G. A.; Sono, M. Tetrahedron Lett. 1998, 54, 9289. (d) Malpass, J. R.; Wallis, A. L. Tetrahedron 1998, 54, 3631. (e) Pearson, A. J.; Srinivasan, K. J. Org. Chem. 1992, 57, 3965.
20. (a) Falk-Heppner, M.; Hugger, U.; Keller, M.; Kaiser, C.; Krieger, R.; Fritz, H.; Prinzbach, H. Liebigs Ann. Recueil 1997, 1481.
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23. For a previous contribution from this laboratory in this area, see: Marco-Contelles, J.; de Opazo, E. Tetrahedron Lett. 1999, 40, 4445.
24. Reviews: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (d) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (e) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833.
25. Reviews: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (d) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (e) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833.
26. Reviews: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (d) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (e) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833.
27. Reviews: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (d) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (e) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833.
28. Reviews: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (d) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (e) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833.
29. The RCM reaction of chiral, polyfunctionalized 1,ω-dienes, leading to cyclopentanes or cyclohexanes, has been reported: (a) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1998, 39, 7987. (b) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 7920. (c) Kornienko, A.; d'Alarcao, M. Tetrahedron: Asymmetry 1999, 10, 827. (d) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853. (e) Kapferer, P.; Sarabia, F.; Vasella, A. Helv. Chim. Acta 1999, 82, 645. (f) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1999, 40, 5063.
30. The RCM reaction of chiral, polyfunctionalized 1,ω-dienes, leading to cyclopentanes or cyclohexanes, has been reported: (a) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1998, 39, 7987. (b) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 7920. (c) Kornienko, A.; d'Alarcao, M. Tetrahedron: Asymmetry 1999, 10, 827. (d) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853. (e) Kapferer, P.; Sarabia, F.; Vasella, A. Helv. Chim. Acta 1999, 82, 645. (f) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1999, 40, 5063.
31. The RCM reaction of chiral, polyfunctionalized 1,ω-dienes, leading to cyclopentanes or cyclohexanes, has been reported: (a) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1998, 39, 7987. (b) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 7920. (c) Kornienko, A.; d'Alarcao, M. Tetrahedron: Asymmetry 1999, 10, 827. (d) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853. (e) Kapferer, P.; Sarabia, F.; Vasella, A. Helv. Chim. Acta 1999, 82, 645. (f) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1999, 40, 5063.
32. The RCM reaction of chiral, polyfunctionalized 1,ω-dienes, leading to cyclopentanes or cyclohexanes, has been reported: (a) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1998, 39, 7987. (b) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 7920. (c) Kornienko, A.; d'Alarcao, M. Tetrahedron: Asymmetry 1999, 10, 827. (d) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853. (e) Kapferer, P.; Sarabia, F.; Vasella, A. Helv. Chim. Acta 1999, 82, 645. (f) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1999, 40, 5063.
33. The RCM reaction of chiral, polyfunctionalized 1,ω-dienes, leading to cyclopentanes or cyclohexanes, has been reported: (a) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1998, 39, 7987. (b) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 7920. (c) Kornienko, A.; d'Alarcao, M. Tetrahedron: Asymmetry 1999, 10, 827. (d) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853. (e) Kapferer, P.; Sarabia, F.; Vasella, A. Helv. Chim. Acta 1999, 82, 645. (f) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1999, 40, 5063.
34. The RCM reaction of chiral, polyfunctionalized 1,ω-dienes, leading to cyclopentanes or cyclohexanes, has been reported: (a) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1998, 39, 7987. (b) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 7920. (c) Kornienko, A.; d'Alarcao, M. Tetrahedron: Asymmetry 1999, 10, 827. (d) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853. (e) Kapferer, P.; Sarabia, F.; Vasella, A. Helv. Chim. Acta 1999, 82, 645. (f) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1999, 40, 5063.
35. The synthesis of precursors 1-6 will be described elsewhere.
36. 3).
37. The role of the absolute configuration of the stereocenters around the olefinic bonds and the strong effect of the free hydroxyl versus protected O-groups in the RCM reactions have been observed before: (a) Hammer, K.; Undheim, K. Tetrahedron 1997, 53, 5925. (b) Efskind, J.; Romming, C.; Undheim, K. J. Chem. Soc., Perkin Trans. 1 1999, 1677. (c) Hammer, K.; Romming, C.; Undheim, K. Tetrahedron 1998, 54, 10837. (d) Holt, D. J.; Barker, W. D.; Jenkins, P. R.; Davies, D. L.; Garratt, S.; Fawcett, J.; Russell, D. R.; Ghosh, S. Angew. Chem., Int. Ed. 1998, 37, 3298.
38. The role of the absolute configuration of the stereocenters around the olefinic bonds and the strong effect of the free hydroxyl versus protected O-groups in the RCM reactions have been observed before: (a) Hammer, K.; Undheim, K. Tetrahedron 1997, 53, 5925. (b) Efskind, J.; Romming, C.; Undheim, K. J. Chem. Soc., Perkin Trans. 1 1999, 1677. (c) Hammer, K.; Romming, C.; Undheim, K. Tetrahedron 1998, 54, 10837. (d) Holt, D. J.; Barker, W. D.; Jenkins, P. R.; Davies, D. L.; Garratt, S.; Fawcett, J.; Russell, D. R.; Ghosh, S. Angew. Chem., Int. Ed. 1998, 37, 3298.
39. The role of the absolute configuration of the stereocenters around the olefinic bonds and the strong effect of the free hydroxyl versus protected O-groups in the RCM reactions have been observed before: (a) Hammer, K.; Undheim, K. Tetrahedron 1997, 53, 5925. (b) Efskind, J.; Romming, C.; Undheim, K. J. Chem. Soc., Perkin Trans. 1 1999, 1677. (c) Hammer, K.; Romming, C.; Undheim, K. Tetrahedron 1998, 54, 10837. (d) Holt, D. J.; Barker, W. D.; Jenkins, P. R.; Davies, D. L.; Garratt, S.; Fawcett, J.; Russell, D. R.; Ghosh, S. Angew. Chem., Int. Ed. 1998, 37, 3298.
40. The role of the absolute configuration of the stereocenters around the olefinic bonds and the strong effect of the free hydroxyl versus protected O-groups in the RCM reactions have been observed before: (a) Hammer, K.; Undheim, K. Tetrahedron 1997, 53, 5925. (b) Efskind, J.; Romming, C.; Undheim, K. J. Chem. Soc., Perkin Trans. 1 1999, 1677. (c) Hammer, K.; Romming, C.; Undheim, K. Tetrahedron 1998, 54, 10837. (d) Holt, D. J.; Barker, W. D.; Jenkins, P. R.; Davies, D. L.; Garratt, S.; Fawcett, J.; Russell, D. R.; Ghosh, S. Angew. Chem., Int. Ed. 1998, 37, 3298.