Stereoselective synthesis of (-)-swainsonine and 1,2-di-epi-swainsonine from γ-hydroxy-α,β-unsaturated sulfones

Synlett

Volumn , Issue 1, 2000, Pages 53-56

  De Vicente, Javier ^b   Gomez Arrayás, Ramón ^b   Cañada, Javier ^a   Carretero, Juan Carlos ^b  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Glycosidase inhibitors; Lipases; Stereoselectivity; Sulfones; Swainsonine

Indexed keywords

GLYCOSIDASE INHIBITOR; MANNOSIDASE; SULFONE DERIVATIVE; SWAINSONINE; SWAINSONINE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; DRUG ACTIVITY; ENANTIOMER; ENZYME INHIBITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0343384128     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (46)

1. a) Guengerich, F. P.; DiMari, S. J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055.
2. b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29. Swainsonine was later found in the plants Swainsona canescens (Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257) and Astragalus letiginosus (Molyneux, R. J.; James, L. F. Science 1982, 216, 190) and also in the fungus Metarhizium anisopliae (Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K.; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 38, 926).
3. b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29. Swainsonine was later found in the plants Swainsona canescens (Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257) and Astragalus letiginosus (Molyneux, R. J.; James, L. F. Science 1982, 216, 190) and also in the fungus Metarhizium anisopliae (Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K.; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 38, 926).
4. b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29. Swainsonine was later found in the plants Swainsona canescens (Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257) and Astragalus letiginosus (Molyneux, R. J.; James, L. F. Science 1982, 216, 190) and also in the fungus Metarhizium anisopliae (Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K.; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 38, 926).
5. b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29. Swainsonine was later found in the plants Swainsona canescens (Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257) and Astragalus letiginosus (Molyneux, R. J.; James, L. F. Science 1982, 216, 190) and also in the fungus Metarhizium anisopliae (Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K.; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 38, 926).
6. See, for instance, Tulsiani, D. R. P.; Harris, T. M.; Touster, O. J. Biol. Chem. 1982, 257, 7936. For a review concerning the synthesis and biological activity of swainsonine and other glycosidase inhibitors, see: Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol. 10, pp 495-583.
7. See, for instance, Tulsiani, D. R. P.; Harris, T. M.; Touster, O. J. Biol. Chem. 1982, 257, 7936. For a review concerning the synthesis and biological activity of swainsonine and other glycosidase inhibitors, see: Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol. 10, pp 495-583.
8. See, for instance, a) Kino, T.; Inamura, N.; Nakahara, K.; Kiyoto, S.; Goto, T.; Terano, H.; Kohsaka, M. J. Antibiot. 1985, 38, 936.
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10. Das, P. C.; Roberts, J. D.; White, S. L.; Olden, K. Oncology Res. 1995, 7, 425.
11. For some recent syntheses of (-)-swainsonine, see: a) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112.
12. b) Ferreira, F.; Greck, C.; Genêt, J. P. Bull. Soc. Chim. Fr. 1997, 134, 615.
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19. i) Ikota, N.; Hanaki, A. Chem. Pharm. Bull 1990, 38, 2712.
20. a) Carretero, J. C.; Gomez Arrayás, R.; Storch de Gracia, I. Tetrahedron Lett. 1996, 37, 3379.
21. b) Carretero, J. C.; Gómez Arrayás, R. J. Org. Chem. 1998, 63, 2993.
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23. d) Carretero, J. C.; Gómez Arrayás, R. Synlett 1999, 49.
24. Although some stereoisomers of (-)-swainsonine are known, to the best of our knowledge 1,2-di-epi-swainsonine had not been previously described.
25. Recently Mukai et al. have described a synthesis of (±)-swainsonine in which the last step was the stereoselective dihydroxylation of an olefin of type A (R = TBDMS), see: Mukai, C.; Sugimoto, Y.-I.; Miyazawa, K.; Yamaguchi, S.; Hanaoka, M. J. Org. Chem. 1998, 63, 6281.
26. Synthesis of (+)-swainsonine, see: a) Oishi, T.; Iwakuma, T.; Hirama, M.; Itô, S. Synlett 1995, 404.
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28. Synthesis of (-)-8,8a-di-epi-swainsonine, see: a) reference 8a.
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31. d) Tadano, K.; Morita, M.; Hotta, Y.; Ogawa, S.; Winchester, B.; Cenci di Bello, I. J. Org. Chem. 1988, 53, 5209.
32. a) Domínguez, E.; Carretero, J. C. Tetrahedron 1990, 46, 7197.
33. b) Trost, B. M.; Grese, T. A. J. Org. Chem. 1991, 56, 3189.
34. Carretero, J. C.; Domínguez, E. J. Org. Chem. 1992, 57, 3867.
35. Chiracel OD column (n-hexane/isopropanol 96:4 as eluent). Retention times of 82 min and 96 min for (S)-2 and (R)-2, respectively.
36. 3N, toluene, -78°C] afforded a 50:50 mixture of trans/cis piperidines.
37. 3) δ: 131.6, 128.2, 74.2, 72.0, 57.9, 48.8, 34.3, 24.0, 18.2, 12.6.
38. The stereochemical assignment of 7 has been established by NMR, mainly by NOESY experiments (see figure below).
39. A similar stereoselectivity has also been found in the dihydroxylation of related unsaturated pyrrolizidines (ref. 5c). In contrast, an opposite stereoselectivity has been described for the dihydroxylation of the TBDMS derivative of (±)-8b (ref. 7). Interestingly, the 80:20 mixture of 9a+10a has been converted in three steps into the epoxide 13 (figure below), which should be a valuable intermediate for the synthesis of trans diols at C1-C2.
40. 2Si 311.2281, found 311.2276.
41. D Lit (ref. 4d) = -80.5 (MeOH, c 0.25).
42. D Lit. (ref. 9d) = -21.2 (MeOH, c 0.78).
43. Schneider, M. J.; Ungemach, F. S.; Broquist, H. P., Harris, T. M. Tetrahedron 1983, 39, 29.
44. Estimated assuming a competitive inhibition process (as it is usually the case for swainsonine and stereoisomers).
45. 50 between 1.75μM and 8μ,M have been reported for the inhibition of α-D-mannosidase (jack bean), see: a) Schneider, M. J., Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29.
46. b) Fleet, G. W. J.; Smith, P. W.; Evans, S. V.; Fellows, L. E. J. Chem. Soc., Chem. Commun. 1984, 1240.