Synthesis of 2,6-Dideoxysugars via Ring-Closing Olefinic Metathesis

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3875-3878

  Andreana, Peter R ^a   McLellan, Jason S ^a   Chen, Yongchen ^a   Wang, Peng George ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; LACTONE; MONOSACCHARIDE;

ARTICLE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKENES; CYCLIZATION; LACTONES; MONOSACCHARIDES; STEREOISOMERISM;

EID: 0038680323     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026710m     Document Type: Article

References (38)

1. For recent reviews see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (b) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. Jorgensen, M.; Hadwiger, P.; Madsen, R.; Stutz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (e) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (h) Blechert, S.; Schuster, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
2. For recent reviews see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (b) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. Jorgensen, M.; Hadwiger, P.; Madsen, R.; Stutz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (e) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (h) Blechert, S.; Schuster, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
3. For recent reviews see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (b) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. Jorgensen, M.; Hadwiger, P.; Madsen, R.; Stutz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (e) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (h) Blechert, S.; Schuster, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
4. For recent reviews see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (b) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. Jorgensen, M.; Hadwiger, P.; Madsen, R.; Stutz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (e) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (h) Blechert, S.; Schuster, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
5. For recent reviews see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (b) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. Jorgensen, M.; Hadwiger, P.; Madsen, R.; Stutz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (e) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (h) Blechert, S.; Schuster, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
6. For recent reviews see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (b) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. Jorgensen, M.; Hadwiger, P.; Madsen, R.; Stutz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (e) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (h) Blechert, S.; Schuster, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
7. For recent reviews see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (b) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. Jorgensen, M.; Hadwiger, P.; Madsen, R.; Stutz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (e) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (h) Blechert, S.; Schuster, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
8. For recent reviews see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (b) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. Jorgensen, M.; Hadwiger, P.; Madsen, R.; Stutz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (e) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (h) Blechert, S.; Schuster, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
9. (a) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
10. (b) Fu, G. C.; Nguyen, S. B. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857.
11. Nyguyen S. B. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858-9859.
12. For α,β-unsaturated γ-lactones see: (a) Furstner, A.; Dierkes, T. Org. Lett. 2000, 2, 2463-2465. For α,β-unsaturated γ-and δ-lactones see: (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 17, 1743-1744. (d) Nicolaou, K. C.; Rodriguez, R. M.; Mitchell, H. J.; van Delft, F. L. Angew. Chem., Int. Ed. 1998, 37, 1874-1876. (e) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654.
13. For α,β-unsaturated γ-lactones see: (a) Furstner, A.; Dierkes, T. Org. Lett. 2000, 2, 2463-2465. For α,β-unsaturated γ-and δ-lactones see: (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 17, 1743-1744. (d) Nicolaou, K. C.; Rodriguez, R. M.; Mitchell, H. J.; van Delft, F. L. Angew. Chem., Int. Ed. 1998, 37, 1874-1876. (e) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654.
14. For α,β-unsaturated γ-lactones see: (a) Furstner, A.; Dierkes, T. Org. Lett. 2000, 2, 2463-2465. For α,β-unsaturated γ-and δ-lactones see: (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 17, 1743-1744. (d) Nicolaou, K. C.; Rodriguez, R. M.; Mitchell, H. J.; van Delft, F. L. Angew. Chem., Int. Ed. 1998, 37, 1874-1876. (e) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654.
15. For α,β-unsaturated γ-lactones see: (a) Furstner, A.; Dierkes, T. Org. Lett. 2000, 2, 2463-2465. For α,β-unsaturated γ-and δ-lactones see: (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 17, 1743-1744. Nicolaou, K. C.; Rodriguez, R. M.; Mitchell, H. J.; van Delft, F. L. Angew. Chem., Int. Ed. 1998, 37, 1874-1876. (e) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654.
16. For α,β-unsaturated γ-lactones see: (a) Furstner, A.; Dierkes, T. Org. Lett. 2000, 2, 2463-2465. For α,β-unsaturated γ-and δ-lactones see: (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 17, 1743-1744. (d) Nicolaou, K. C.; Rodriguez, R. M.; Mitchell, H. J.; van Delft, F. L. Angew. Chem., Int. Ed. 1998, 37, 1874-1876. (e) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654.
17. Kirschning, A.; Bechtholdt, A. F. W.; Rohr, J. Top. Curr. Chem. 1997, 188, 1-84.
18. (a) Ulven, T.; Carlsen, P. H. J. Eur. J. Org. Chem. 2001, 3367-3374 (and references therein).
19. (b) Shafer, C. M.; Molinski, T. F. Carbohydr. Res. 1998, 310, 223-228.
20. Roush, W. R.; Straub, J. A. Tetrahedron Lett. 1986, 27, 3349-3352.
21. Bock, K.; Lundt, I.; Pedersen, C.; Refn, S. Acta Chem. Scand. 1986, B40, 740-744.
22. (e) Roush, W. R.; Brown, J. R. J. Org. Chem. 1983, 48, 5093-5101.
23. (f) Chmielewski, M. Tetrahedron 1979, 35, 2067-2070.
24. Oppolzer, W.; Kuendig, E. P.; Bishop. P. M.; Perret, C. Tetrahedron Lett. 1982, 23, 3901-3904.
25. Harcken, C.; Bruckner, R.; Rank, E. Chem. Eur. J. 1998, 4, 2342-2352.
26. DCC coupling provided the desired ester in high yield but the unwanted dicyclohexylurea byproduct proved difficult to remove.
27. (a) Toste, D. F.; Chatterjee, A. K.; Grubbs, R. H. Pure Appl. Chem. 2002, 74, 7-10.
28. (b) Goldberg, S. D.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 807-810 (and references therein).
29. Sukkari, H. E.; Gesson, J.-P.; Renoux, B. Tetrahedron Lett. 1998, 39, 4043-4046.
30. Furstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130-9136.
31. For the removal of ruthenium byproducts see: (a) Ahn, Y. M.; Yang, K. L.; Georg, G. I. Org. Lett. 2001, 3, 1411-1413. (b) Paquette, L. A.; Schloss, J. D.; Efremov, I.; Fabris, F.; Gallou, F.; Mendez-Andino, J.; Yang, J. Org. Lett. 2000, 2, 1259-1261. Maynard, H. D.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 4137-4140.
32. For the removal of ruthenium byproducts see: (a) Ahn, Y. M.; Yang, K. L.; Georg, G. I. Org. Lett. 2001, 3, 1411-1413. (b) Paquette, L. A.; Schloss, J. D.; Efremov, I.; Fabris, F.; Gallou, F.; Mendez-Andino, J.; Yang, J. Org. Lett. 2000, 2, 1259-1261. Maynard, H. D.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 4137-4140.
33. For the removal of ruthenium byproducts see: (a) Ahn, Y. M.; Yang, K. L.; Georg, G. I. Org. Lett. 2001, 3, 1411-1413. (b) Paquette, L. A.; Schloss, J. D.; Efremov, I.; Fabris, F.; Gallou, F.; Mendez-Andino, J.; Yang, J. Org. Lett. 2000, 2, 1259-1261. Maynard, H. D.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 4137-4140.
34. Reviews: (a) Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547. (b) Johnson, R. A.; Sharpless, K. B. Asymmetric Catalysis in Organic Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 227-272. Lohray, B. B. Tetrahedron: Asymmetry 1992, 3, 1317-1349.
35. Reviews: (a) Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547. (b) Johnson, R. A.; Sharpless, K. B. Asymmetric Catalysis in Organic Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 227-272. Lohray, B. B. Tetrahedron: Asymmetry 1992, 3, 1317-1349.
36. Reviews: (a) Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547. (b) Johnson, R. A.; Sharpless, K. B. Asymmetric Catalysis in Organic Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 227-272. Lohray, B. B. Tetrahedron: Asymmetry 1992, 3, 1317-1349.
37. Preparation of AD mixes: Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X. L. J. Org. Chem. 1992, 57, 2768-2771.
38. Mehltretter, G. M.; Dobler, C.; Sundermeier, U.; Beller, M. Tetrahedron Lett. 2000, 41, 8083-8087.