Stereoselective glycosylations of a family of 6-deoxy-1,2-glycals generated by catalytic alkynol cycloisomerization

Journal of the American Chemical Society

Volumn 122, Issue 18, 2000, Pages 4304-4309

  McDonald, Frank E ^a   Reddy, K Subba ^a   Díaz, Yolanda ^a,b  

^a EMORY UNIVERSITY   (United States)

^b UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

6 DEOXY 1,2 GLYCAL DERIVATIVE; DEXTRO DIGITOXOSE BETA 4 DEXTRO DIGITOXOSE GLYCAL; GLYCOSIDE; IODOACETIC ACID; OLIGOSACCHARIDE; TUNGSTEN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DIASTEREOISOMER; GLYCOSYLATION; ISOMERISM; PHOTOLYSIS; STEREOCHEMISTRY;

EID: 0034630891     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994229u     Document Type: Article

References (45)

1. Kirschning, A.; Bechthold, A. F.-W.; Rohr, J. Top. Curr. Chem. 1997, 188, 1.
2. Cardiac Glycosides, Part 1: Experimental Pharmacology. In Handbook Exp. Pharmacol. 1981, vol. 56.
3. (a) Wohlert, S. E.; Künzel, E.; Machinek, R.; Mendéz, C.; Salas, J. A.; Rohr, J. J. Nat. Prod. 1999, 62, 119.
4. (b) Thiem, J.; Meyer, B. Tetrahedron 1981, 37, 551.
5. (c) Thiem, J.; Meyer, B. J. Chem. Soc., Perkin Trans. 2 1979, 1331.
6. (d) Berlin, Y. A.; Esipov, S. E.; Kolosov, M. N.; Shemyakin, M. M. Tetrahedron Lett. 1966, 7, 1431; 1643.
7. (a) Olafsdottir, E. S.; Cornett, C.; Jaroszewski, J. W. Acta Chem. Scand. 1989, 43, 51.
8. (b) Yoshikawa, M.; Murakami, T.; Shimada, H.; Fukude, N.; Matsuda, H.; Sashida, Y.; Yamahara, J. Heterocycles 1998, 48, 869.
9. (a) Neupert-Laves, K.; Dobler M. Helv. Chim. Acta 1981, 65, 262.
10. (b) Kawai, H.; Hayakawa, Y.; Nakagawa, M.; Furihata, K.; Seto, H.; Otake, N. Tetrahedron Left. 1984, 25, 1937; 1941.
11. McDonald, F. E.; Zhu, H. Y. H. Tetrahedron 1997, 53, 11061.
12. McDonald, F. E.; Zhu, H. Y. H. J. Am. Chem. Soc. 1998, 120, 4246.
13. Merault, G.; Bourgeois, P.; Dunogues, J.; Duffaut, N. J. Organomet. Chem. 1974, 76, 17.
14. (a) Parker, K. A.; Ledeboer, M. W. J. Org. Chem. 1996, 61, 3214.
15. (b) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1986.
16. (c) Garcia, J.; Lopez, M.; Romeu, J. Synlett 1999, 429.
17. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
18. (a) Mitsunobu, O. Synthesis 1981, 1.
19. (b) Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017.
20. (c) Hughes, D. L.; Reamer, R. A. J. Org. Chem. 1996, 61, 2967.
21. (a) Herzig, J.; Nudelman, A.; Gottlieb, H. E.; Fischer, B. J. Org. Chem. 1986, 51, 727.
22. (b) Alzeev, A.; Vasella, A. Helv. Chim. Acta 1995, 78, 177.
23. 3 is not required for the removal of alkynylsilanes from our substrates.
24. Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557.
25. D = +53.9) obtained in two steps from 3,4-di-O-acetyl-L-rhamnal: (a) NaOMe, MeOH; (b) TBDMSCl, imidazole, DMF. This also establishes the absolute configuration of all glycals 10-13 and confirms absolute and relative stereoinduction in the preparation of epoxyalkynol 2.
26. Cycloisomerizations of substrates 6 and 7 (leading to glycals ribo-10 and lyxo-11) are facile and proceed in nearly quantitative yields, whereas the cyclization of 8a/b to arabino-glycals 12a/b is slightly slower. Substrates 9a/b leading to xylo-glycals 13a/b proceed in satisfactory yield but in all cases approximately 10% of exo-cyclization product is formed along with the major endo-cyclization products 13a/b.
27. (a) McDonald, F. E.; Bowman, J. L. J. Org. Chem. 1998, 63, 3680.
28. (b) McDonald, F. E.; Zhu, H. Y. H. Tetrahedron 1997, 53, 11061.
29. Prepared from 4 in 83% yield: TBDMSCl (1.0 equiv), imidazole (2.0 equiv). DMF.
30. Toshima, K.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1988, 61, 2369.
31. (a) Kaila, N.; Blumenstein, M.; Bielawska, H.; Franck, R. W. J. Org. Chem. 1992, 57, 4576.
32. (b) Franck, R. W.; Kaila, N.; Blumenstein, M.; Geer, A.; Huang, X. L.; Dannenberg, J. J. J. Org. Chem. 1993, 58, 5335.
33. (c) Bolitt, V.; Mioskowski, C.; Lee, S.-G.; Falck, J. R. J. Org. Chem. 1990, 55, 5812.
34. (a) Roush, W. R.; Briner, K.; Sebesta, D. P. Synlett 1993, 264.
35. (b) Roush, W. R.; Bennett, C. E. J. Am. Chem. Soc. 1999, 121, 3541.
36. (c) Roush, W. R.; Narayan, S. Org. Lett. 1999, 1, 899. For representative direct iodoglycosylations, see:
37. (d) Thiem, J.; Karl, H.; Schwentner, J. Synthesis 1978, 696.
38. (e) Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656.
39. (a) Kirschning, A.; Plumeier, C.; Rose, L. Chem. Commun. 1998, 33.
40. (b) Kirschning, A.; Jesberger, M.; Monenschein, H. Tetrahedron Lett. 1999, 40, 8999.
41. Roush, W. R.; Narayan, S.; Bennett, C. E.; Briner, K. Org. Lett. 1999, 1, 895.
42. Kirschning, A. Eur. J. Org. Chem. 1998, 63, 2267.
43. The use of TMSOTf gave slightly lower yields of glycosylation products along with byproduct arising from loss of the TBDMS protective group.
44. Similar behavior has been observed with 2-phenylseleno-l-O-acetate mixtures derived from arabino-glycal 12a: Dräger, G.; Garming, A.; Maul, C.; Noltemeyer, M.; Thiericke, R.; Zerlin, M.; Kirschning, A. Chem. Eur. J. 1998, 4, 1324.
45. Similar behavior has been observed in C-glycosylations of 2,6-dideoxyglucosyl fluorides: Hosoya, T.; Ohashi, Y.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1996, 37, 663.