Use of heterocycles as chiral ligands and auxiliaries in asymmetric syntheses of sphingosine, sphingofungins B and F

Tetrahedron

Volumn 54, Issue 35, 1998, Pages 10275-10294

  Kobayashi, Shu ^a   Furuta, Takayuki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; LIGAND; SPHINGOFUNGIN B; SPHINGOFUNGIN F; SPHINGOLIPID; SPHINGOSINE; SPHINGOSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DIASTEREOISOMER; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0032572894     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00484-0     Document Type: Article

References (54)

1. 1) (a) Kanfer, J. N.; Hakomori, S. Sphingolipid Biochemistry; Plenum Press: New York, 1983.
2. (b) Hannun, Y. A. J. Biol. Chem. 1994, 269, 3125.
3. 2) Hannun, Y. A.; Loomis, C. R.; Merrill, A. H., Jr.; Bell, R. M. J. Biol. Chem. 1986, 261, 12604.
4. 3) Reviews: (a) Merrill, A. H., Jr.; Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins and Membranes, Vance, D. E., Vance, J., Eds; Elsevier Science B. V.: Amsterdam, 1996, pp 309-339.
5. (b) Hannun, Y. A. Science 1996, 274, 1855.
6. 4) See also, (a) Hannun, Y. A.; Loomis, C. R.; Merrill, A. H. Jr.; Bell, R. M. J. Biol. Chem. 1986, 261, 12604.
7. (b) Okazaki, T.; Bell, R. M.; Hannun, Y. A. J. Biol. Chem. 1989, 264, 19076.
8. (c) Hanada, K., Nishijima, M., Kiso, M., Hasegawa, A., Fujita, S., Ogawa, T., and Akamatsu, Y. J. Biol. Chem. 1992, 267, 23527.
9. (d) Zhang, H.; Desai, N. N.; Olivera, A.; Seki, T.; Brooker, G.; Spiegel, S. J. Cell Biol. 1991, 114, 155.
10. (e) Wang, E.; Norred, W. P.; Bacon, C. W.; Riley, R. T.; Merrill, A. H., Jr. J. Biol. Chem. 1991, 266, 14486.
11. (f) Obeid, L. M.; Linardic, C. M.; Karolak, L. A.; Hannun, Y. A. Science 1993, 259, 1769.
12. (g) Joseph, C. K.; Wright, S. D.; Borainann, W. G.; Randolph, J. T.; Kumar, E. R.; Bittman, R.; Liu, J.; Kolesnick, R. N. J. Biol. Chem. 1994, 269, 17606.
13. (h) Wiegmann, K.; Schutze, S.; Machleidt, T.; Witte, D.; Kronke, M. Cell 1994, 78, 1005.
14. (i) Miyake, Y.; Koizumi, Y.; Nakamura, S.; Fujita, T.; Kawasaki, T. Biochem. Biophys. Res. Commun. 1995, 211, 396.
15. (j) Pinto, W. J., Wells, G. W., Lester, R. L. J. Bacteriol. 1992, 174, 2575.
16. 5) (a) VanMiddlesworth, F.; Giacobbe, R. A.; Lopez, M.; Garrity, G.; Bland, J. A.; Bartizal, K.; Fromtling, R. A.; Polishook, J.; Zweerink, M.; Edison, A. M.; Rozdilsky, W.; Wilson, K. E.; Monaghan, R. L. J. Antibiot. 1992, 45, 861.
17. (b) Zweerink, M. M.; Edison, A. M.; Well, G. B.; Pinto, W.; Lester, R. L. J. Biol. Chem. 1992, 267, 25032. Structure elucidation,
18. (c) VanMiddlesworth, F.; Dufresne, C.; Wincott, F. E.; Mosley, R. T.; Wilson, K. E. Tetrahedron Lett. 1992, 33, 297.
19. 6) Preliminary reports, (a) Kobayashi, S.; Hayashi, T.; Kawasuji, T. Tetrahedron Lett. 1994, 35, 9573.
20. (b) Kobayashi, S.; Hayashi, T.; Iwamoto, S.; Furuta, T.; Matsumura, M. Synlett 1996, 672.
21. (c) Kobayashi, S.; Matsumura, M.; Furuta, T.; Hayashi, T.; Iwamoto, S. Synlett 1997, 301. As for synthesis of sphingofungins and their biological activity as potent inhibitors of serine palmitoyltransferase (SPT),
22. (d) Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. in press.
23. 7) (a) Kobayashi, S.; Kawasuji, T. Synlett 1993, 911.
24. (b) Kobayashi, S.; Kawasuji, T, Mori, N. Chem. Lett. 1994, 217.
25. 8) Boeckman, R. K., Jr.; Thomas, E. W. J. Am. Chem. Soc. 1987, 100, 2806.
26. 9) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663.
27. 10) Lewbart, M. L.; Schneider, J. J. J. Org. Chem. 1969, 34, 3505.
28. 11) Dong, Z.; Butcher, J. A., Jr. Tetrahedron Lett. 1991, 32, 5291.
29. 12) For synthesis of D-erythro-sphingosine and/or phytosphingosine, ex, (a) Spanu, P.; Rassu, G.; Pinna, L.; Battistini, L.; Casiraghi, G. Tetrahedron: Asym. 1997, 8, 3237.
30. (b) Murakami, T.; Hato, M. J. Chem. Soc., Perkin 1 1996, 823.
31. (c) Li, Y.-L.; Wu, Y.-L. Liebig Ann. Chem. 1996, 2079.
32. (d) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382, and references cited therein.
33. 13) Cf. Mori, K.; Uenishi, K. Liebig Ann. Chem. 1994, 41.
34. 14) Kishida, E.; Kasahara, M.; Takagi, Y.; Matsumura, M.; Hayashi, T.; Kobayashi, S.; Masuzawa, Y. J. Lipid Med. Cell Sign. 1997, 16, 127.
35. 15) As for the previous synthesis of shingofungins, (a) Mori, K.; Otaka, K. Tetrahedron Lett. 1994, 35, 9207.
36. (b) Chida, N.; Ikemoto, H.; Noguchi, A.; Amano, S.; Ogawa, S. Natural Product Lett. 1995, 6, 295.
37. 16) Rossi, R.; Carpita, A. Synthesis 1977, 561.
38. 17) (a) Schöllkopf, U. Pure Appl. Chem. 1983, 55, 1799 (1983).
39. (b) Schöllkopf, U.; Hartwig, W.; Groth, U.; Westphalen, K. Liebigs Ann. Chem. 1981, 696.
40. 18) (a) Cram, D. J.; Abd Elhafez, F. A. J. Am. Chem. Soc. 1952, 74, 5828.
41. (b) Karabatsos, G. J. J. Am. Chem. Soc. 1967, 59, 1367.
42. (c) Chrest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
43. (d) Anh N. T.; Eisenstein, O. Nouv. J. Chim., 1977, 1, 61.
44. 19) Cf. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 556.
45. 20) Cf. Ruiz, M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1996, 37, 5743.
46. 21) Kurosawa, K.; Ohfune, Y. J. Am. Chem. Soc. 1986, 108, 6041. We are grateful to Professor Y. Ohfune for helpful discussion on isolation of sphingofungin B.
47. 22) We are grateful to Drs. N. Yasuda, K. E. Wilson, O. Hensens, and I. Shinkai (Merck Research Laboratories) for providing us with an authentic sample of sphingofungin B and spectral data.
48. 23) Horn, W. S.; Smith, J. L.; Bills, G. F.; Raghoobar, S. L.; Helms, G. L.; Kurtz, M. B.; Marrinan, J. A.; Frommer, B. R.; Thoraton, R. A.; Mandala, S. M. J. Antibiotics 1992, 45, 1692.
49. 24) (a) Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371.
50. (b) Kobayashi, S. Synlett 1994, 689.
51. 25) (a) Batchelor, R. J.; Ruddick, J. N. R.; Sams, J. R.; Aubke, F. Inorg. Chem. 1977, 16, 1414.
52. (b) Mukaiyama, T.; Iwasawa, N.; Stevens, R. W.; Haga, T. Tetrahedron 1984, 40, 1381.
53. 26) (a) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247.
54. (b) Mukaiyama, T.; Kobayashi, S.; Sano, T. Tetrahedron 1990, 46, 4653.