Stereoselective synthesis of tetrahydrofurans and linear methyl enol- ethers from glycals

Carbohydrate Research

Volumn 306, Issue 1-2, 1998, Pages 221-230

  Bettelli, Enzo ^a   D'Andrea, Piero ^a   Mascanzoni, Stefano ^a   Passacantilli, Pietro ^a   Piancatelli, Giovanni ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

2,5 Anhydro sugars; Glycals; Glycosyl glycals; Synthesis, linear methyl enol ethers; Synthesis, tetrahydrofurans; Thallium(III) nitrate

Indexed keywords

ACETAL DERIVATIVE; ARABINITOL; BENZENE DERIVATIVE; CELLOBIOSE; ETHER DERIVATIVE; GALACTOSE; GLUCOSE; LACTOSE; MANNOSE; MELIBIOSE; METHYL GROUP; REAGENT; RHAMNOSE; SODIUM BOROHYDRIDE; TETRAHYDROFURAN; THALLIUM;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CIS TRANS ISOMERISM; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031800053     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(97)10062-3     Document Type: Article

References (23)

1. S. Hanessian, Total Synthesis of Natural Products. The Chiron Approach, Oxford, 1983, pp. 40-183; H. Kunz and K. Rück, Angew. Chem., Int. Ed. Engl., 32 (1993) 336-358; S.J. Danishefsky and M.T. Bilodeau, Angew. Chem., Int. Ed. Engl., 35 (1996) 1381-1419; T.L. Boivin, Tetrahedron, 43 (1987) 3309-3362; G. Cardillo and M. Orena, Tetrahedron, 46 (1990) 3321-3408.
2. S. Hanessian, Total Synthesis of Natural Products. The Chiron Approach, Oxford, 1983, pp. 40-183; H. Kunz and K. Rück, Angew. Chem., Int. Ed. Engl., 32 (1993) 336-358; S.J. Danishefsky and M.T. Bilodeau, Angew. Chem., Int. Ed. Engl., 35 (1996) 1381-1419; T.L. Boivin, Tetrahedron, 43 (1987) 3309-3362; G. Cardillo and M. Orena, Tetrahedron, 46 (1990) 3321-3408.
3. S. Hanessian, Total Synthesis of Natural Products. The Chiron Approach, Oxford, 1983, pp. 40-183; H. Kunz and K. Rück, Angew. Chem., Int. Ed. Engl., 32 (1993) 336-358; S.J. Danishefsky and M.T. Bilodeau, Angew. Chem., Int. Ed. Engl., 35 (1996) 1381-1419; T.L. Boivin, Tetrahedron, 43 (1987) 3309-3362; G. Cardillo and M. Orena, Tetrahedron, 46 (1990) 3321-3408.
4. S. Hanessian, Total Synthesis of Natural Products. The Chiron Approach, Oxford, 1983, pp. 40-183; H. Kunz and K. Rück, Angew. Chem., Int. Ed. Engl., 32 (1993) 336-358; S.J. Danishefsky and M.T. Bilodeau, Angew. Chem., Int. Ed. Engl., 35 (1996) 1381-1419; T.L. Boivin, Tetrahedron, 43 (1987) 3309-3362; G. Cardillo and M. Orena, Tetrahedron, 46 (1990) 3321-3408.
5. S. Hanessian, Total Synthesis of Natural Products. The Chiron Approach, Oxford, 1983, pp. 40-183; H. Kunz and K. Rück, Angew. Chem., Int. Ed. Engl., 32 (1993) 336-358; S.J. Danishefsky and M.T. Bilodeau, Angew. Chem., Int. Ed. Engl., 35 (1996) 1381-1419; T.L. Boivin, Tetrahedron, 43 (1987) 3309-3362; G. Cardillo and M. Orena, Tetrahedron, 46 (1990) 3321-3408.
6. J. Wengel, J. Lau, and E.B. Pedersen, Chem. Scr., 29 (1989) 67-70; A.G. Tolstikov, N.V. Khakhalina, and L. Spirikhin, Synthesis, (1988) 221-222; S. Yik-Kai Tam and B. Fraser-Reid, Carbohydr. Res., 25 (1975) 29-43.
7. J. Wengel, J. Lau, and E.B. Pedersen, Chem. Scr., 29 (1989) 67-70; A.G. Tolstikov, N.V. Khakhalina, and L. Spirikhin, Synthesis, (1988) 221-222; S. Yik-Kai Tam and B. Fraser-Reid, Carbohydr. Res., 25 (1975) 29-43.
8. J. Wengel, J. Lau, and E.B. Pedersen, Chem. Scr., 29 (1989) 67-70; A.G. Tolstikov, N.V. Khakhalina, and L. Spirikhin, Synthesis, (1988) 221-222; S. Yik-Kai Tam and B. Fraser-Reid, Carbohydr. Res., 25 (1975) 29-43.
9. A. Kaye, S. Neidle, and C.B. Reese, Tetrahedron Lett., 29 (1988) 1841-1844; P. Passacantilli, Tetrahedron Lett., 30 (1989) 5349-5352; D.B. Tulshian and B. Fraser-Reid, J. Am. Chem. Soc., 103 (1981) 474- 475; A. McKillop and E.C. Taylor, in G. Wilkinson, F.G.A. Stone, and E.W. Abel (Ed.), Comprehensive Organometallic Chemistry, Vol. 7, Pergamon Press, Oxford, 1982, pp. 490-493.
10. A. Kaye, S. Neidle, and C.B. Reese, Tetrahedron Lett., 29 (1988) 1841-1844; P. Passacantilli, Tetrahedron Lett., 30 (1989) 5349-5352; D.B. Tulshian and B. Fraser-Reid, J. Am. Chem. Soc., 103 (1981) 474- 475; A. McKillop and E.C. Taylor, in G. Wilkinson, F.G.A. Stone, and E.W. Abel (Ed.), Comprehensive Organometallic Chemistry, Vol. 7, Pergamon Press, Oxford, 1982, pp. 490-493.
11. A. Kaye, S. Neidle, and C.B. Reese, Tetrahedron Lett., 29 (1988) 1841-1844; P. Passacantilli, Tetrahedron Lett., 30 (1989) 5349-5352; D.B. Tulshian and B. Fraser-Reid, J. Am. Chem. Soc., 103 (1981) 474-475; A. McKillop and E.C. Taylor, in G. Wilkinson, F.G.A. Stone, and E.W. Abel (Ed.), Comprehensive Organometallic Chemistry, Vol. 7, Pergamon Press, Oxford, 1982, pp. 490-493.
12. A. Kaye, S. Neidle, and C.B. Reese, Tetrahedron Lett., 29 (1988) 1841-1844; P. Passacantilli, Tetrahedron Lett., 30 (1989) 5349-5352; D.B. Tulshian and B. Fraser-Reid, J. Am. Chem. Soc., 103 (1981) 474- 475; A. McKillop and E.C. Taylor, in G. Wilkinson, F.G.A. Stone, and E.W. Abel (Ed.), Comprehensive Organometallic Chemistry, Vol. 7, Pergamon Press, Oxford, 1982, pp. 490-493.
13. W. Roth and W. Pigman, Methods Carbohydr. Chem., 2 (1963) 405-408; F. Shafidazeh, Methods Carbohydr. Chem., 2 (1963) 409-410; I.D. Blackburne, P.M. Fredericks, and R.D. Guthrie, Aust. J. Chem., 29 (1976) 381-391.
14. W. Roth and W. Pigman, Methods Carbohydr. Chem., 2 (1963) 405-408; F. Shafidazeh, Methods Carbohydr. Chem., 2 (1963) 409-410; I.D. Blackburne, P.M. Fredericks, and R.D. Guthrie, Aust. J. Chem., 29 (1976) 381-391.
15. W. Roth and W. Pigman, Methods Carbohydr. Chem., 2 (1963) 405-408; F. Shafidazeh, Methods Carbohydr. Chem., 2 (1963) 409-410; I.D. Blackburne, P.M. Fredericks, and R.D. Guthrie, Aust. J. Chem., 29 (1976) 381-391.
16. W.N. Haworth, E.L. Hirst, M.M.T. Plant, and R.J.W. Reynolds, J. Chem. Soc., (1930) 2644-2653; P.W. Kent and S.D. Dimitrijevich, J. Fluorine Chem., 10 (1977) 455-478; W. Kinzy and R.R. Schmidt, Carbohydr. Res., 164 (1987) 265-276.
17. W.N. Haworth, E.L. Hirst, M.M.T. Plant, and R.J.W. Reynolds, J. Chem. Soc., (1930) 2644-2653; P.W. Kent and S.D. Dimitrijevich, J. Fluorine Chem., 10 (1977) 455-478; W. Kinzy and R.R. Schmidt, Carbohydr. Res., 164 (1987) 265-276.
18. W.N. Haworth, E.L. Hirst, M.M.T. Plant, and R.J.W. Reynolds, J. Chem. Soc., (1930) 2644-2653; P.W. Kent and S.D. Dimitrijevich, J. Fluorine Chem., 10 (1977) 455-478; W. Kinzy and R.R. Schmidt, Carbohydr. Res., 164 (1987) 265-276.
19. P.C. Ting and P.A. Bartlett, J. Am. Chem. Soc., 106 (1984) 2668-2671.
20. D. Horton and K.D. Philips, Carbohydr. Res., 30 (1973) 367-374.
21. S. Danishefsky and M.T. Bilodeau, Angew. Chem., Int. Ed. Engl., 35 (1996), 1380-1419.
22. A. Bianco, The Chemistry of Iridoids, in Atta-Ur. Rahman (Ed.), Studies in Natural Products, Chemistry, Vol. 7, Elsevier, 1990, pp. 439-477.
23. G. Carnevale, E. Davini, C Javarone, and C. Trogolo, J. Chem. Soc., Perkin Trans, 1, (1990) 989-992.