Improved Syntheses of (+)-Lentiginosine and (1S,2S,7R,8aS)-Trihydroxyoctahydroindolizine by Butenol Cycloaddition to Enantiopure Protected Dihydroxy Pyrroline N-Oxides

Synlett

Volumn 1996, Issue 8, 1996, Pages 761-763

  Goti, Andrea ^a   Cardona, Francesca ^a   Brandi, Alberto ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0342563709     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5508     Document Type: Article

References (33)

1. (a) Cordero, F. M.; Cicchi, S.; Goti, A.; Brandi, A. Tetrahedron Lett. 1994, 35, 949.
2. (b) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806.
3. Isolation: Pastuszak, I.; Molyneux, R. J.; James, L. F.; Elbein, A. D. Biochemistry 1990, 29, 1886.
4. Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymmetry 1996, 7, in press.
5. Castanospermine: Saul, R.; Chambers, J. P.; Molyneux, R. J.; Elbein, A. D. Arch. Biochem. Biophys. 1983, 221, 593.
6. Brandi, A.; Cordero, F. M.; Goti, A.; De Sarlo, F.; Guarna, A. Synlett 1993, 1.
7. (b) Goti, A.; Cordero, F. M.; Brandi, A. Top. Curr. Chem. 1996, 178, 1.
8. For therapeutic potentiality of glycosidases inhibitors, see the following and references cited therein. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199. Antibiotic: Ishida, N.; Kumagai, K.; Niida, T.; Tsuruoka, T.; Yumoto, H. J. Antibiot., Ser. A 1967, 20, 66. Anti-HIV: Sunkara, P. S.; Taylor, D. L.; Kang, M. S.; Bowlin, T. L.; Liu, P. S.; Tyms, A. S.; Sjoerdsma, A. Lancet 1989, 1206. Anticancer: Dennis, J. W.; Koch, K.; Beckner, D. J. Nat. Cancer Inst. 1989, 81, 1028. Antidiabetes: Leonhardt, W.; Hanefield, M.; Fischer, S.; Schulze, J. European J. Clin. Invest. 1994, 24, Suppl. 3, 45.
9. For therapeutic potentiality of glycosidases inhibitors, see the following and references cited therein. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199. Antibiotic: Ishida, N.; Kumagai, K.; Niida, T.; Tsuruoka, T.; Yumoto, H. J. Antibiot., Ser. A 1967, 20, 66. Anti-HIV: Sunkara, P. S.; Taylor, D. L.; Kang, M. S.; Bowlin, T. L.; Liu, P. S.; Tyms, A. S.; Sjoerdsma, A. Lancet 1989, 1206. Anticancer: Dennis, J. W.; Koch, K.; Beckner, D. J. Nat. Cancer Inst. 1989, 81, 1028. Antidiabetes: Leonhardt, W.; Hanefield, M.; Fischer, S.; Schulze, J. European J. Clin. Invest. 1994, 24, Suppl. 3, 45.
10. For therapeutic potentiality of glycosidases inhibitors, see the following and references cited therein. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199. Antibiotic: Ishida, N.; Kumagai, K.; Niida, T.; Tsuruoka, T.; Yumoto, H. J. Antibiot., Ser. A 1967, 20, 66. Anti-HIV: Sunkara, P. S.; Taylor, D. L.; Kang, M. S.; Bowlin, T. L.; Liu, P. S.; Tyms, A. S.; Sjoerdsma, A. Lancet 1989, 1206. Anticancer: Dennis, J. W.; Koch, K.; Beckner, D. J. Nat. Cancer Inst. 1989, 81, 1028. Antidiabetes: Leonhardt, W.; Hanefield, M.; Fischer, S.; Schulze, J. European J. Clin. Invest. 1994, 24, Suppl. 3, 45.
11. For therapeutic potentiality of glycosidases inhibitors, see the following and references cited therein. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199. Antibiotic: Ishida, N.; Kumagai, K.; Niida, T.; Tsuruoka, T.; Yumoto, H. J. Antibiot., Ser. A 1967, 20, 66. Anti-HIV: Sunkara, P. S.; Taylor, D. L.; Kang, M. S.; Bowlin, T. L.; Liu, P. S.; Tyms, A. S.; Sjoerdsma, A. Lancet 1989, 1206. Anticancer: Dennis, J. W.; Koch, K.; Beckner, D. J. Nat. Cancer Inst. 1989, 81, 1028. Antidiabetes: Leonhardt, W.; Hanefield, M.; Fischer, S.; Schulze, J. European J. Clin. Invest. 1994, 24, Suppl. 3, 45.
12. For therapeutic potentiality of glycosidases inhibitors, see the following and references cited therein. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199. Antibiotic: Ishida, N.; Kumagai, K.; Niida, T.; Tsuruoka, T.; Yumoto, H. J. Antibiot., Ser. A 1967, 20, 66. Anti-HIV: Sunkara, P. S.; Taylor, D. L.; Kang, M. S.; Bowlin, T. L.; Liu, P. S.; Tyms, A. S.; Sjoerdsma, A. Lancet 1989, 1206. Anticancer: Dennis, J. W.; Koch, K.; Beckner, D. J. Nat. Cancer Inst. 1989, 81, 1028. Antidiabetes: Leonhardt, W.; Hanefield, M.; Fischer, S.; Schulze, J. European J. Clin. Invest. 1994, 24, Suppl. 3, 45.
13. Other syntheses of (+)-lentiginosine: (a) Yoda, H.; Kitayama, H.; Katagiri, T.; Takabe, K. Tetrahedron: Asymmetry 1993, 4, 1455. (b) Gurjar, M. K.; Ghosh, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871. (c) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (d) Giovannini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1995, 60, 5706.
14. Other syntheses of (+)-lentiginosine: (a) Yoda, H.; Kitayama, H.; Katagiri, T.; Takabe, K. Tetrahedron: Asymmetry 1993, 4, 1455. (b) Gurjar, M. K.; Ghosh, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871. (c) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (d) Giovannini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1995, 60, 5706.
15. Other syntheses of (+)-lentiginosine: (a) Yoda, H.; Kitayama, H.; Katagiri, T.; Takabe, K. Tetrahedron: Asymmetry 1993, 4, 1455. (b) Gurjar, M. K.; Ghosh, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871. (c) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (d) Giovannini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1995, 60, 5706.
16. Other syntheses of (+)-lentiginosine: (a) Yoda, H.; Kitayama, H.; Katagiri, T.; Takabe, K. Tetrahedron: Asymmetry 1993, 4, 1455. (b) Gurjar, M. K.; Ghosh, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871. (c) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (d) Giovannini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1995, 60, 5706.
17. (a) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem. 1993, 58, 5274.
18. (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316.
19. (a) Tufariello J. J. Acc. Chem. Res. 1979, 12, 396.
20. (b) Tufariello, J. J.; Tette, J. P. J. Org. Chem. 1975, 40, 3866.
21. (c) Tufariello, J. J.; Tegeler, J. J. Tetrahedron Lett. 1976, 45, 4037.
22. Mc Caig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939.
23. All new compounds gave satisfactory spectral and/or analytical data.
24. 4: C, 63.76; H, 10.37; N, 4.65. Found: C, 63.36; H, 10.43; N, 4.87.
25. 3: C, 67.33; H, 10.95; N, 4.91. Found: C, 67.70; H, 11.20; N, 4.78.
26. (a) Grob, C. A.; Ostermayer, F.; Raudenbusch, W. Helv. Chim. Acta 1962, 45, 1672.
27. (b) Grob, C. A.; Schwarz, W. Helv. Chim. Acta 1964, 47, 1870.
28. (a) Bottini, A. T.; Grob, C. A.; Schumacher, E.; Zergenyi, J. Helv. Chim. Acta 1966, 49, 2516.
29. (b) Geisel, M.; Grob, C. A.; Wohl, R. A. Helv. Chim. Acta 1969, 52, 2206.
30. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
31. 13C NMR: δ 183.1 (s), 136.8 (d), 130.6 (d), 117.8 (d), 83.2 (d), 81.4 (d), 77.8 (d), 73.9 (s), 73.8 (s), 65.0 (d), 60.8 (t), 49.8 (t), 33.2 (t), 29.4 (t), 29.1 (q, 3 C), 28.6 (q, 3 C).
32. 2: C, 71.33; H, 11.60; N, 5.20. Found: C, 71.48; H, 11.80; N, 4.82.
33. Jefford, C. W.; Tang, Q.; Zaslona, A. Helv. Chim. Acta 1989, 72, 1749.