Polyannulated glycopyranosides via radical-mediated tandem reactions, stereoselective synthesis of 6-5-6 dioxatricycles via 5-exo-trig, 6-endo-dig mode - III.

Tetrahedron

Volumn 53, Issue 25, 1997, Pages 8383-8400

  Hoffmann, H M R ^a   Herden, U ^a   Breithor, M ^a   Rhode, O ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOPYRANOSIDE;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 0030909306     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00518-8     Document Type: Article

References (35)

1. General reviews on sequential reactions: Ho, T.-L. Tandem Organic Reactions, Wiley, New York, 1992; Tietze, L. F. Chem. Rev. 1996, 96, 115; see also Hoffmann, H. M. R. Angew. Chem. Int. Ed. Engl. 1992, 31, 1332.
2. General reviews on sequential reactions: Ho, T.-L. Tandem Organic Reactions, Wiley, New York, 1992; Tietze, L. F. Chem. Rev. 1996, 96, 115; see also Hoffmann, H. M. R. Angew. Chem. Int. Ed. Engl. 1992, 31, 1332.
3. General reviews on sequential reactions: Ho, T.-L. Tandem Organic Reactions, Wiley, New York, 1992; Tietze, L. F. Chem. Rev. 1996, 96, 115; see also Hoffmann, H. M. R. Angew. Chem. Int. Ed. Engl. 1992, 31, 1332.
4. For radical mediated annulations of glycals see Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 113, 5791; Lopez, J. C.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 3450; Pak, H.; Dickson, J. K., Jr.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5337; Dickson, J. K., Jr.; Tsang, R.; Llera, J. M.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5350; Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57; DeMesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T.; Hug, P.; Winkler, T. Synlett 1990, 687 and preceding work; RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139.
5. For radical mediated annulations of glycals see Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 113, 5791; Lopez, J. C.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 3450; Pak, H.; Dickson, J. K., Jr.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5337; Dickson, J. K., Jr.; Tsang, R.; Llera, J. M.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5350; Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57; DeMesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T.; Hug, P.; Winkler, T. Synlett 1990, 687 and preceding work; RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139.
6. For radical mediated annulations of glycals see Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 113, 5791; Lopez, J. C.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 3450; Pak, H.; Dickson, J. K., Jr.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5337; Dickson, J. K., Jr.; Tsang, R.; Llera, J. M.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5350; Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57; DeMesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T.; Hug, P.; Winkler, T. Synlett 1990, 687 and preceding work; RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139.
7. For radical mediated annulations of glycals see Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 113, 5791; Lopez, J. C.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 3450; Pak, H.; Dickson, J. K., Jr.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5337; Dickson, J. K., Jr.; Tsang, R.; Llera, J. M.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5350; Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57; DeMesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T.; Hug, P.; Winkler, T. Synlett 1990, 687 and preceding work; RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139.
8. For radical mediated annulations of glycals see Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 113, 5791; Lopez, J. C.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 3450; Pak, H.; Dickson, J. K., Jr.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5337; Dickson, J. K., Jr.; Tsang, R.; Llera, J. M.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5350; Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57; DeMesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T.; Hug, P.; Winkler, T. Synlett 1990, 687 and preceding work; RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139.
9. For radical mediated annulations of glycals see Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 113, 5791; Lopez, J. C.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 3450; Pak, H.; Dickson, J. K., Jr.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5337; Dickson, J. K., Jr.; Tsang, R.; Llera, J. M.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5350; Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57; DeMesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T.; Hug, P.; Winkler, T. Synlett 1990, 687 and preceding work; RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139.
10. For radical mediated annulations of glycals see Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 113, 5791; Lopez, J. C.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 3450; Pak, H.; Dickson, J. K., Jr.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5337; Dickson, J. K., Jr.; Tsang, R.; Llera, J. M.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5350; Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57; DeMesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T.; Hug, P.; Winkler, T. Synlett 1990, 687 and preceding work; RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139.
11. Albrecht, U.; Wartchow, R.; Hoffmann, H. M. R. Angew. Chem. 1992, 104, 903; Angew. Chem. Int. Ed. 1992, 31, 903. Palladium-mediated annulations: Nguefack, J.-F.; Bolitt, V.; Sinou, D. J. Org. Chem. 1997, 62, 1341.
12. Albrecht, U.; Wartchow, R.; Hoffmann, H. M. R. Angew. Chem. 1992, 104, 903; Angew. Chem. Int. Ed. 1992, 31, 903. Palladium-mediated annulations: Nguefack, J.-F.; Bolitt, V.; Sinou, D. J. Org. Chem. 1997, 62, 1341.
13. Albrecht, U.; Wartchow, R.; Hoffmann, H. M. R. Angew. Chem. 1992, 104, 903; Angew. Chem. Int. Ed. 1992, 31, 903. Palladium-mediated annulations: Nguefack, J.-F.; Bolitt, V.; Sinou, D. J. Org. Chem. 1997, 62, 1341.
14. For substituent effects in iodine atom transfer on exocyclic vinylic radicals see Curran, D. P.; Chen, M.-H.; Kim, D. J. Am. Chem. Soc. 1989, 111, 6265 and references therein.
15. Thiem, J.; Karl, H.; Schwentner, J. Synthesis 1978, 696; Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834, Jung, M. E.; Choe, S. W. T. Tetrahedron Lett. 1993, 34, 6247.
16. Thiem, J.; Karl, H.; Schwentner, J. Synthesis 1978, 696; Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834, Jung, M. E.; Choe, S. W. T. Tetrahedron Lett. 1993, 34, 6247.
17. Thiem, J.; Karl, H.; Schwentner, J. Synthesis 1978, 696; Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834, Jung, M. E.; Choe, S. W. T. Tetrahedron Lett. 1993, 34, 6247.
18. Nicolaou, K. C.; Zipkin, R. E.; Petasis, N. A. J. Am. Chem. Soc. 1982, 104, 5558.
19. Nozaki, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 2547.
20. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389; Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 770, 7536.
21. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389; Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 770, 7536.
22. For a specific discussion of tandem free radical cyclizations see Curran, D. P. in Comprehensive Organic-Chemistry (Eds.: Trost, B. M.; Fleming, I.), Vol. 4 (Ed.: Semmelhack, M. F.), Oxford, 1991, 715-778 Radical Addition Reactions and 779-831 Radical Cyclizations and Sequential Radical Reactions, see also Hart, D. J. Science 1984, 223, 883; for monographs on radical reactions see Motherwell, W. B.; Crich, D. Best Synthetic Methods. Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1991; Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon, Oxford, 1986 General radical cyclization reactions see Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856; Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
23. For a specific discussion of tandem free radical cyclizations see Curran, D. P. in Comprehensive Organic-Chemistry (Eds.: Trost, B. M.; Fleming, I.), Vol. 4 (Ed.: Semmelhack, M. F.), Oxford, 1991, 715-778 Radical Addition Reactions and 779-831 Radical Cyclizations and Sequential Radical Reactions, see also Hart, D. J. Science 1984, 223, 883; for monographs on radical reactions see Motherwell, W. B.; Crich, D. Best Synthetic Methods. Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1991; Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon, Oxford, 1986 General radical cyclization reactions see Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856; Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
24. For a specific discussion of tandem free radical cyclizations see Curran, D. P. in Comprehensive Organic-Chemistry (Eds.: Trost, B. M.; Fleming, I.), Vol. 4 (Ed.: Semmelhack, M. F.), Oxford, 1991, 715-778 Radical Addition Reactions and 779-831 Radical Cyclizations and Sequential Radical Reactions, see also Hart, D. J. Science 1984, 223, 883; for monographs on radical reactions see Motherwell, W. B.; Crich, D. Best Synthetic Methods. Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1991; Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon, Oxford, 1986 General radical cyclization reactions see Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856; Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
25. For a specific discussion of tandem free radical cyclizations see Curran, D. P. in Comprehensive Organic-Chemistry (Eds.: Trost, B. M.; Fleming, I.), Vol. 4 (Ed.: Semmelhack, M. F.), Oxford, 1991, 715-778 Radical Addition Reactions and 779-831 Radical Cyclizations and Sequential Radical Reactions, see also Hart, D. J. Science 1984, 223, 883; for monographs on radical reactions see Motherwell, W. B.; Crich, D. Best Synthetic Methods. Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1991; Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon, Oxford, 1986 General radical cyclization reactions see Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856; Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
26. For a specific discussion of tandem free radical cyclizations see Curran, D. P. in Comprehensive Organic-Chemistry (Eds.: Trost, B. M.; Fleming, I.), Vol. 4 (Ed.: Semmelhack, M. F.), Oxford, 1991, 715-778 Radical Addition Reactions and 779-831 Radical Cyclizations and Sequential Radical Reactions, see also Hart, D. J. Science 1984, 223, 883; for monographs on radical reactions see Motherwell, W. B.; Crich, D. Best Synthetic Methods. Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1991; Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon, Oxford, 1986 General radical cyclization reactions see Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856; Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
27. For a specific discussion of tandem free radical cyclizations see Curran, D. P. in Comprehensive Organic-Chemistry (Eds.: Trost, B. M.; Fleming, I.), Vol. 4 (Ed.: Semmelhack, M. F.), Oxford, 1991, 715-778 Radical Addition Reactions and 779-831 Radical Cyclizations and Sequential Radical Reactions, see also Hart, D. J. Science 1984, 223, 883; for monographs on radical reactions see Motherwell, W. B.; Crich, D. Best Synthetic Methods. Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1991; Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon, Oxford, 1986 General radical cyclization reactions see Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856; Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
28. Herden, U.; Hoffmann, H. M. R.; Wartchow, R. Z. Kristallogr. 1997, 272, in press
29. Breithor, M.; Hoffmann, H. M. R.; Wartchow, R. Z. Kristallogr. 1997, 272, 251.
30. Less reactive electrophiles such as carbon dioxide and also methyl and ethyl chloroformate were less efficient in trapping the vinyllithium intermediate.
31. Hill, K.; von Rybinski, W.; Stoll, G. Alkyl Polyglycosides. Technology, Properties and Applications, VCH, Weinheim, 1997.
32. Review: Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem. 1995, 107, 453-474; 569-593; Angew. Chem. Int. Ed. Engl. 1995, 34, 412; 521.
33. Review: Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem. 1995, 107, 453-474; 569-593; Angew. Chem. Int. Ed. Engl. 1995, 34, 412; 521.
34. Review: Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem. 1995, 107, 453-474; 569-593; Angew. Chem. Int. Ed. Engl. 1995, 34, 412; 521.
35. Review: Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem. 1995, 107, 453-474; 569-593; Angew. Chem. Int. Ed. Engl. 1995, 34, 412; 521.