Synthesis of acosamine and daunosamine from sugar δ-enelactones

Tetrahedron

Volumn 53, Issue 2, 1997, Pages 739-746

  Socha, Dariusz ^a   Jurczak, Margarita ^a   Chmielewski, Marek ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ACOSAMINE; DAUNOSAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031013413     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01016-2     Document Type: Article

References (25)

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12. Hauser, F.M.; Ellenberger, S.R. Chem. Rev., 1986, 35-67; Pelyvas, I.F.; Monneret, C.; Herczegh, P.; Synthetic Aspects of Aminodeoxy Sugars of Antibiotics, Springer-Verlag, Berlin, 1988; Thomas, G.J. in Recent Progress in the Chemical Synthesis of Antibiotics, Eds Lukacs, G.; Ohno, M. Springer-Verlag, Berlin 1990, 467-496, Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Organic Synthesis Highligts, Verlag Chemie, Weinheim, 1991, 351-358; Wade, P.A.; Appa Rao, J; James, F.; Bereznak, F.; Yuan, C.-K. Tetrahedron Letters, 1989, 30, 5969-5972; Abbaci, B .; Florent J.-K.; Monneret, C. Bull. Soc. Chim. France, 1989, 5, 667-672; Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron, 1990, 46, 4823-4846; Sammes, P.G.; Thertford, D.; J. Chem. Soc. Perkin Trans. I, 1988, 111-123; Ha, D.-C.; Hart, D.J.; Tetrahedron, 1987, 28, 4489-4492; Hiyama, T.; Kobayashi, K.; Nishido, K.; Bull. Chem. Soc. Jpn., 1987, 60, 2127-2137; Hirama, M; Shigemoto, T.; Itô, S. J. Org. Chem., 1987, 52, 3342-3346, Monneret, C.; Gagnet, R.; Florent, J.-C. J. Carbohydr. Chem., 1987, 6, 221-229; Paulus, H.W., Fraser-Reid, B. Carbohydr. Res., 1986, 150, 111-119; Jurczak, J.; Kozak, J.; Gołȩbiowski, A.; Tetrahedron, 1992, 48, 4231-4238;
13. Hauser, F.M.; Ellenberger, S.R. Chem. Rev., 1986, 35-67; Pelyvas, I.F.; Monneret, C.; Herczegh, P.; Synthetic Aspects of Aminodeoxy Sugars of Antibiotics, Springer-Verlag, Berlin, 1988; Thomas, G.J. in Recent Progress in the Chemical Synthesis of Antibiotics, Eds Lukacs, G.; Ohno, M. Springer-Verlag, Berlin 1990, 467-496, Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Organic Synthesis Highligts, Verlag Chemie, Weinheim, 1991, 351-358; Wade, P.A.; Appa Rao, J; James, F.; Bereznak, F.; Yuan, C.-K. Tetrahedron Letters, 1989, 30, 5969-5972; Abbaci, B .; Florent J.-K.; Monneret, C. Bull. Soc. Chim. France, 1989, 5, 667-672; Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron, 1990, 46, 4823-4846; Sammes, P.G.; Thertford, D.; J. Chem. Soc. Perkin Trans. I, 1988, 111-123; Ha, D.-C.; Hart, D.J.; Tetrahedron, 1987, 28, 4489-4492; Hiyama, T.; Kobayashi, K.; Nishido, K.; Bull. Chem. Soc. Jpn., 1987, 60, 2127-2137; Hirama, M; Shigemoto, T.; Itô, S. J. Org. Chem., 1987, 52, 3342-3346, Monneret, C.; Gagnet, R.; Florent, J.-C. J. Carbohydr. Chem., 1987, 6, 221-229; Paulus, H.W., Fraser-Reid, B. Carbohydr. Res., 1986, 150, 111-119; Jurczak, J.; Kozak, J.; Gołȩbiowski, A.; Tetrahedron, 1992, 48, 4231-4238;
14. Hauser, F.M.; Ellenberger, S.R. Chem. Rev., 1986, 35-67; Pelyvas, I.F.; Monneret, C.; Herczegh, P.; Synthetic Aspects of Aminodeoxy Sugars of Antibiotics, Springer-Verlag, Berlin, 1988; Thomas, G.J. in Recent Progress in the Chemical Synthesis of Antibiotics, Eds Lukacs, G.; Ohno, M. Springer-Verlag, Berlin 1990, 467-496, Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Organic Synthesis Highligts, Verlag Chemie, Weinheim, 1991, 351-358; Wade, P.A.; Appa Rao, J; James, F.; Bereznak, F.; Yuan, C.-K. Tetrahedron Letters, 1989, 30, 5969-5972; Abbaci, B .; Florent J.-K.; Monneret, C. Bull. Soc. Chim. France, 1989, 5, 667-672; Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron, 1990, 46, 4823-4846; Sammes, P.G.; Thertford, D.; J. Chem. Soc. Perkin Trans. I, 1988, 111-123; Ha, D.-C.; Hart, D.J.; Tetrahedron, 1987, 28, 4489-4492; Hiyama, T.; Kobayashi, K.; Nishido, K.; Bull. Chem. Soc. Jpn., 1987, 60, 2127-2137; Hirama, M; Shigemoto, T.; Itô, S. J. Org. Chem., 1987, 52, 3342-3346, Monneret, C.; Gagnet, R.; Florent, J.-C. J. Carbohydr. Chem., 1987, 6, 221-229; Paulus, H.W., Fraser-Reid, B. Carbohydr. Res., 1986, 150, 111-119; Jurczak, J.; Kozak, J.; Gołȩbiowski, A.; Tetrahedron, 1992, 48, 4231-4238;
15. Hauser, F.M.; Ellenberger, S.R. Chem. Rev., 1986, 35-67; Pelyvas, I.F.; Monneret, C.; Herczegh, P.; Synthetic Aspects of Aminodeoxy Sugars of Antibiotics, Springer-Verlag, Berlin, 1988; Thomas, G.J. in Recent Progress in the Chemical Synthesis of Antibiotics, Eds Lukacs, G.; Ohno, M. Springer-Verlag, Berlin 1990, 467-496, Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Organic Synthesis Highligts, Verlag Chemie, Weinheim, 1991, 351-358; Wade, P.A.; Appa Rao, J; James, F.; Bereznak, F.; Yuan, C.-K. Tetrahedron Letters, 1989, 30, 5969-5972; Abbaci, B .; Florent J.-K.; Monneret, C. Bull. Soc. Chim. France, 1989, 5, 667-672; Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron, 1990, 46, 4823-4846; Sammes, P.G.; Thertford, D.; J. Chem. Soc. Perkin Trans. I, 1988, 111-123; Ha, D.-C.; Hart, D.J.; Tetrahedron, 1987, 28, 4489-4492; Hiyama, T.; Kobayashi, K.; Nishido, K.; Bull. Chem. Soc. Jpn., 1987, 60, 2127-2137; Hirama, M; Shigemoto, T.; Itô, S. J. Org. Chem., 1987, 52, 3342-3346, Monneret, C.; Gagnet, R.; Florent, J.-C. J. Carbohydr. Chem., 1987, 6, 221-229; Paulus, H.W., Fraser-Reid, B. Carbohydr. Res., 1986, 150, 111-119; Jurczak, J.; Kozak, J.; Gołȩbiowski, A.; Tetrahedron, 1992, 48, 4231-4238;
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19. Hauser, F.M.; Ellenberger, S.R. Chem. Rev., 1986, 35-67; Pelyvas, I.F.; Monneret, C.; Herczegh, P.; Synthetic Aspects of Aminodeoxy Sugars of Antibiotics, Springer-Verlag, Berlin, 1988; Thomas, G.J. in Recent Progress in the Chemical Synthesis of Antibiotics, Eds Lukacs, G.; Ohno, M. Springer-Verlag, Berlin 1990, 467-496, Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Organic Synthesis Highligts, Verlag Chemie, Weinheim, 1991, 351-358; Wade, P.A.; Appa Rao, J; James, F.; Bereznak, F.; Yuan, C.-K. Tetrahedron Letters, 1989, 30, 5969-5972; Abbaci, B .; Florent J.-K.; Monneret, C. Bull. Soc. Chim. France, 1989, 5, 667-672; Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron, 1990, 46, 4823-4846; Sammes, P.G.; Thertford, D.; J. Chem. Soc. Perkin Trans. I, 1988, 111-123; Ha, D.-C.; Hart, D.J.; Tetrahedron, 1987, 28, 4489-4492; Hiyama, T.; Kobayashi, K.; Nishido, K.; Bull. Chem. Soc. Jpn., 1987, 60, 2127-2137; Hirama, M; Shigemoto, T.; Itô, S. J. Org. Chem., 1987, 52, 3342-3346, Monneret, C.; Gagnet, R.; Florent, J.-C. J. Carbohydr. Chem., 1987, 6, 221-229; Paulus, H.W., Fraser-Reid, B. Carbohydr. Res., 1986, 150, 111-119; Jurczak, J.; Kozak, J.; Gołȩbiowski, A.; Tetrahedron, 1992, 48, 4231-4238;
20. Hauser, F.M.; Ellenberger, S.R. Chem. Rev., 1986, 35-67; Pelyvas, I.F.; Monneret, C.; Herczegh, P.; Synthetic Aspects of Aminodeoxy Sugars of Antibiotics, Springer-Verlag, Berlin, 1988; Thomas, G.J. in Recent Progress in the Chemical Synthesis of Antibiotics, Eds Lukacs, G.; Ohno, M. Springer-Verlag, Berlin 1990, 467-496, Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Organic Synthesis Highligts, Verlag Chemie, Weinheim, 1991, 351-358; Wade, P.A.; Appa Rao, J; James, F.; Bereznak, F.; Yuan, C.-K. Tetrahedron Letters, 1989, 30, 5969-5972; Abbaci, B .; Florent J.-K.; Monneret, C. Bull. Soc. Chim. France, 1989, 5, 667-672; Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron, 1990, 46, 4823-4846; Sammes, P.G.; Thertford, D.; J. Chem. Soc. Perkin Trans. I, 1988, 111-123; Ha, D.-C.; Hart, D.J.; Tetrahedron, 1987, 28, 4489-4492; Hiyama, T.; Kobayashi, K.; Nishido, K.; Bull. Chem. Soc. Jpn., 1987, 60, 2127-2137; Hirama, M; Shigemoto, T.; Itô, S. J. Org. Chem., 1987, 52, 3342-3346, Monneret, C.; Gagnet, R.; Florent, J.-C. J. Carbohydr. Chem., 1987, 6, 221-229; Paulus, H.W., Fraser-Reid, B. Carbohydr. Res., 1986, 150, 111-119; Jurczak, J.; Kozak, J.; Gołȩbiowski, A.; Tetrahedron, 1992, 48, 4231-4238;
21. Hauser, F.M.; Ellenberger, S.R. Chem. Rev., 1986, 35-67; Pelyvas, I.F.; Monneret, C.; Herczegh, P.; Synthetic Aspects of Aminodeoxy Sugars of Antibiotics, Springer-Verlag, Berlin, 1988; Thomas, G.J. in Recent Progress in the Chemical Synthesis of Antibiotics, Eds Lukacs, G.; Ohno, M. Springer-Verlag, Berlin 1990, 467-496, Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Organic Synthesis Highligts, Verlag Chemie, Weinheim, 1991, 351-358; Wade, P.A.; Appa Rao, J; James, F.; Bereznak, F.; Yuan, C.-K. Tetrahedron Letters, 1989, 30, 5969-5972; Abbaci, B .; Florent J.-K.; Monneret, C. Bull. Soc. Chim. France, 1989, 5, 667-672; Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron, 1990, 46, 4823-4846; Sammes, P.G.; Thertford, D.; J. Chem. Soc. Perkin Trans. I, 1988, 111-123; Ha, D.-C.; Hart, D.J.; Tetrahedron, 1987, 28, 4489-4492; Hiyama, T.; Kobayashi, K.; Nishido, K.; Bull. Chem. Soc. Jpn., 1987, 60, 2127-2137; Hirama, M; Shigemoto, T.; Itô, S. J. Org. Chem., 1987, 52, 3342-3346, Monneret, C.; Gagnet, R.; Florent, J.-C. J. Carbohydr. Chem., 1987, 6, 221-229; Paulus, H.W., Fraser-Reid, B. Carbohydr. Res., 1986, 150, 111-119; Jurczak, J.; Kozak, J.; Gołȩbiowski, A.; Tetrahedron, 1992, 48, 4231-4238;
22. Hauser, F.M.; Ellenberger, S.R. Chem. Rev., 1986, 35-67; Pelyvas, I.F.; Monneret, C.; Herczegh, P.; Synthetic Aspects of Aminodeoxy Sugars of Antibiotics, Springer-Verlag, Berlin, 1988; Thomas, G.J. in Recent Progress in the Chemical Synthesis of Antibiotics, Eds Lukacs, G.; Ohno, M. Springer-Verlag, Berlin 1990, 467-496, Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Organic Synthesis Highligts, Verlag Chemie, Weinheim, 1991, 351-358; Wade, P.A.; Appa Rao, J; James, F.; Bereznak, F.; Yuan, C.-K. Tetrahedron Letters, 1989, 30, 5969-5972; Abbaci, B .; Florent J.-K.; Monneret, C. Bull. Soc. Chim. France, 1989, 5, 667-672; Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron, 1990, 46, 4823-4846; Sammes, P.G.; Thertford, D.; J. Chem. Soc. Perkin Trans. I, 1988, 111-123; Ha, D.-C.; Hart, D.J.; Tetrahedron, 1987, 28, 4489-4492; Hiyama, T.; Kobayashi, K.; Nishido, K.; Bull. Chem. Soc. Jpn., 1987, 60, 2127-2137; Hirama, M; Shigemoto, T.; Itô, S. J. Org. Chem., 1987, 52, 3342-3346, Monneret, C.; Gagnet, R.; Florent, J.-C. J. Carbohydr. Chem., 1987, 6, 221-229; Paulus, H.W., Fraser-Reid, B. Carbohydr. Res., 1986, 150, 111-119; Jurczak, J.; Kozak, J.; Gołȩbiowski, A.; Tetrahedron, 1992, 48, 4231-4238;
23. Chmielewski, M.; Jurczak, M.; Maciejewski, S.; Carbohydr. Res., 1987, 165, 111-115
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