C-6 allylated pyranosides for the synthesis of complex oxygenated tetrahydrofurans

Tetrahedron

Volumn 53, Issue 16, 1997, Pages 5711-5724

  Seepersaud, Mohindra ^a   Blumenstein, Michael ^a   Mootoo, David R ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030972666     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00282-2     Document Type: Article

References (35)

1. For general approaches to 3-hydroxylated-THF's. see: (a) Tamaru, Y.; Hojo, M.; Kawamura, S.; Sawada, S.; Yoshida, Z. J. Org. Chem. 1987, 52, 4062-4072.
2. (b) Cha, J. K.; Kim, Y. -G. Tetrahedron Lett. 1988, 29, 2011-2014.
3. (c) Grese, T. A.; Hutchinson, K. D.; Overman, L. E. J. Org. Chem. 1993, 58, 2468-2477.
4. (d) Osumi, K.; Sugimura, H. Tetrahedron Lett., 1995, 36, 5789-5792.
5. (e) Andrey, O.; Landais, Y. Tetrahedron Lett. 1993, 34, 8435-8438.
6. For recent examples of the use of 3-hydroxylated-THF's in the synthesis of complex polyethers, see: (a) Semmelhack, M. F.; Epa, W. R.; Cheung, W. -H.; Gu, Y.; Kim, C.; Zhang, N.; Lew, W. J. Am. Chem.Soc. 1994, 116, 7455-7456.
7. (b) Cooper, A. J.; Pan, W.; Salomon, R. G. Tetrahedron Lett. 1993, 34, 8193-8196.
8. For examples of related electrophilic cyclizations and discussions on stereoselectivity see: (a) Chamberlin, A.R.; Mulholland, Jr., R.L.; Kahn, S.D.; Hehre, W.J. J. Am. Chem. Soc. 1987, 109, 672-677.
9. (b) Reitz, A. B.; Nortey, S. O.; Maryanoff, B. E.; Liotta, D.; Monahan, III R. J. Org. Chem. 1987, 52, 4191-4202.
10. (c) Labelle, M.; Morton, H. E.; Guindon, Y.; Springer, J. P. J. Am. Chem. Soc. 1988, 110, 4533-4540; Labelle, M.; Guindon, Y. J. Am. Chem. Soc. 1989, 111, 2204-2210.
11. (c) Labelle, M.; Morton, H. E.; Guindon, Y.; Springer, J. P. J. Am. Chem. Soc. 1988, 110, 4533-4540; Labelle, M.; Guindon, Y. J. Am. Chem. Soc. 1989, 111, 2204-2210.
12. For examples of allylic stereocontrol in other reaction types, see: epoxidation: Rossiter, B.E.; Verhoeven, T. R.; Sharpless, K. B. Tetrahedron Lett., 1979 20, 4733-4736.
13. (b) osmylation: Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett., 1983, 24, 3943-3946, 3947-3950.
14. (c) hydroboration: Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487-2489.
15. (d) cyclopropanation: Mulzer, J.; Kappert, M. Angew. Chem. Int. Ed. Engl. 1983, 22, 63-64.
16. (e) nitrile oxide cycloaddition: Houk, K. N.; Moses, S.R.; Wu, Y.-D.; Rondan, N. G.; Jager, V.; Schohe, R.; Fronczek, F. R. J. Am. Chem. Soc. 1984, 106, 3880-3882.
17. Although the cyclization of hydroxy-epoxide precursors provides a highly versatile strategy for the preparation of 2,5-dialkyl THF's the related approach to 2,5-dialkyl-3-hydroxylated THF's from penten-1,3-diol-epoxides is not well known. (a) Hoye, T.R.; Tan, L. Tetrahedron Lett. 1995, 36, 1981-1984.
18. (b) Hashimoto, M.; Harigaya, H.; Yanagiya, M.; Shirahama, H. J. Org. Chem. 1991, 56, 2299-2311.
19. Zhang, H.; Wilson, P.; Shan, W.; Ruan, Z.; Mootoo, D.R. Tetrahedron Lett. 1995, 36, 649-652; Ruan, Z.; Wilson, P.; Mootoo, D.R. Tetrahedron Lett. 1996, 37, 3619-3622.
20. Zhang, H.; Wilson, P.; Shan, W.; Ruan, Z.; Mootoo, D.R. Tetrahedron Lett. 1995, 36, 649-652; Ruan, Z.; Wilson, P.; Mootoo, D.R. Tetrahedron Lett. 1996, 37, 3619-3622.
21. Suzuki, T.; Koizumi, K.; Suzuki, M.; Kurosawa, E.; Chem. Lett. 1983, 1643-1644.
22. For synthetic studies on kumausyne based on 3-hydroxylated-THF precursors, see: (a) Tonn, C. E.; Palazon, J. M.; Ruiz-Perez, C.; Rodriguez, M. L.; Martin, V. S. Tetrahedron Lett. 1995, 36, 5789-5792.
23. (b) ref. 1c-e.
24. For recently discovered eunicellins, see: Roussis, V.; Fenical, W.; Vagias, C.; Kornprobst, J.-M.; Miralles, J. Tetrahedron 1996, 52, 2735-2742.
25. For synthetic studies on the eunicellins, see: MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
26. Isobe, M.; Ichikawa, Y.; Funabashi, Y.; Mio, S.; Goto, T. Tetrahedron 1986, 42, 2863-2872.
27. Pougny, J. -R. Tetrahedron Lett. 1984, 25, 2363-2366.
28. (a) Dale, A. J.; Mosher, S. H. J. Am. Chem. Soc. 1973, 95, 512-519.
29. (b) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
30. (c) Rieser, J. M.; Hui, Y.; Rupprecht, J. K.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L.; Hanson, P. R.; Zhuang, Z.; Hoye, T. J. Am.Chem.Soc. 1992, 114, 10203-10213.
31. Lemieux, R.U.; Morgan, A.R. Can. J. Chem. 1965, 43, 2190-2198.
32. Carbohydrate and THF numbering is used for the pyranoside precursors and the THF products respectively. For easier comparison with our earlier work on 2,5-substituted THF's, the relative stereochemistry of the THF products is designated as 2,5-rather than 2,3-substituted derivatives. For THF's derived from R-allylic alcohol substrates: cis-2,5 = cis-2,3. For THF's derived from S-allylic alcohol substrates: cis-2,5 = trans-2,3.
33. The methylene proton syn to the substitutents on the adjacent carbons generally experiences diamagnetic shielding: Mihelich, E. D.; Hite, G. A. J. Am. Chem. Soc. 1992, 114, 7318-7319 and references cited.
34. For discussions on "matched/mismatched" diastereoselection, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem. Int. Ed. Engl. 1985, 24, 1-76
35. (b) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348-6359.