Synthesis of tetrahydropyrans from sugar lactones

Tetrahedron

Volumn 54, Issue 44, 1998, Pages 13591-13620

  Estevez, Juan C ^a   Fairbanks, Antony J ^b   Fleet, George W J ^b  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Carbohydrates; Lactones; Mitsunobu reactions; Pyrans

Indexed keywords

LACTONE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0032578711     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00837-0     Document Type: Article

References (28)

1. 1. Witty, D.R.; Fleet, G.W.J.; Choi, S.; Vogt, K.; Wilson, F.X.; Wang, Y.; Storer, R.; Myers, P.L.; Wallis, C.J. Tetrahedron Lett. 1990, 31, 6927-6930 and references contained therein.
2. 2. Choi, S.S.; Myerscough, P.M.; Fairbanks, A.J.; Skead, B.M.; Richard, C.J.F.; Mantell, S.J.; Son, J.C.; Fleet, G.W.J.; Saunders, J.; Brown, D. J. Chem. Soc., Chem. Commun. 1992, 1605-1607.
3. 3. Weatley, J.R.; Bichard, C.J.F.; Mantell, S.; Son, J.C.; Hughes, D.J.; Fleet, G.W.J.; Brown, D. J. Chem. Soc., Chem. Commun. 1993, 1065-1067.
4. 4. For a preliminary communication of some of these results see: Estevez, J.C.; Fairbanks, A.J.; Hsia, K.Y.; Ward, P.; Fleet, G.W.J. Tetrahedron Lett. 1994, 35, 3361-3364.
5. 5. For some reviews see: (a) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J.L.; Martín, J.D. Chem. Rev. 1995, 95, 1953-1980;
6. (b) Harmange, J.-C; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711-1754;
7. (c) Boivin, T.L.B. Tetrahedron 1987, 43, 3309-3362.
8. 6. For some recent tetrahydropyran syntheses see: (a) Banwell, M.G.; Bissett, B.D.; Bui, C.T.; Pham, H.T.T.; Simpson, G.W. Aus. J. Chem. 1998, 51, 9-18;
9. (b) Takagi, R.; Sasaoka, A.; Kojima, S.; Ohkata, K. Heterocycles 1997, 45, 2313-2316;
10. (c) Craig, D.C.; Edwards, G.L.; Muldoon, C.A. Synlett 1997, 1318-1320;
11. (d) Schneider, C. Synlett 1997, 815-817;
12. (e) Mori, Y. Chem. Eur. J. 1997, 3, 849-852;
13. (f) Betancort, J.M.; Martin, V.S.; Padrón, J.M.; Palazón, J.M.; Ramírez, M.A.; Soler, M.A. J. Org. Chem. 1997,.62, 4570-4583;
14. (g) Hu, Y.Q.; Skalitzky, D.J.; Rychnovsky, S.D. Tetrahedron Lett. 1996, 37, 8679-8682.
15. 7. For a review on sugar epoxides see: Williams, N.R. Adv. Carbohydr. Chem. Biochem., 1970, 25, 109-179.
16. 8. For a review on 2,5-anhydrosugars see Defaye, J. Adv. Carbohydr. Chem. Biochem., 1970, 25, 181-228.
17. 9. For a general review on anhydroalditols see Soltzberg, S. Adv. Carbohydr. Chem. Biochem., 1970, 25, 229-283.
18. 10. Schmidt, O.T. Methods in Carbohydr. Chem. 1963, 2, 318-325.
19. 11. Åkerfeldt, K.; Bartlett, P.A. Carbohydr. Res. 1986, 755, 137-145.
20. 12. (a) Wood, W.W.; Watson, G.M. J. Chem. Soc., Perkin Trans. 1, 1987, 2681-2688.
21. (b) Sowa, W.; Thomas, G.H. S. Can. J. Chem., 1966, 44, 836-838.
22. 13. (a) Fischer, J.-C.; Horton, D. Carbohydr. Res., 1977, 59, 477-503.
23. (b) Theander, O. Acta Chem. Scand., 1963, 17, 1751-1760.
24. 14. Bichard, C.J.F.; Fairbanks, A.J.; Fleet, G.W.J.; Ramsden, N.G.; Vogt, K.; Doherty, O.; Pearce, L.; Watkin, D.J. Tetrahedron: Asymmetry, 1991, 2, 901-912.
25. 15. Fairbanks, A.J.; Fleet, G.W.J. Tetrahedron 1995, 57, 3881-3894.
26. 16. For a discussion of the stereochemical consequences of oxetane formation by ring contraction reactions see: (a) Witty, D.R.; Fleet, G.W.J.; Vogt, K.; Wilson, F.X.; Wang, Y.; Storer, R.; Myers, P.L.; Wallis, C.J. Tetrahedron Lett. 1990, 31, 4787-4790.
27. (b) Austin, G.N.; Fleet, G.W.J.; Peach, J.M.; Prout, K.; Son, J.C. Tetrahedron Lett. 1987, 28, 4741-4744.
28. 17. Rosenfeld, D.A.; Richtmyer, N.K.; and Hudson, C.S. J. Am. Chem. Soc., 1948, 70, 2201.