A stereocontrolled synthesis of D-erythro-sphingosine and D-ribo-phytosphingsinet [6]

Bulletin of the Korean Chemical Society

Volumn 23, Issue 9, 2002, Pages 1195-1196

  Kang, Sung Ho ^a   Hwang, Yu Sang ^a   Lee, Hee Seung ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

D erythro Sphingosine; D ribo Sphingosine; Amino alcohols

Indexed keywords

PHYTOSPHINGOSINE; SPHINGOSINE DERIVATIVE;

BIOMEDICINE; CELL DIFFERENTIATION; CELL GROWTH; CHEMICAL ANALYSIS; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROLYSIS; LETTER; MOLECULAR DYNAMICS; SIGNAL TRANSDUCTION; STEREOCHEMISTRY;

EID: 0037145169     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2002.23.9.1195     Document Type: Letter

References (48)

1. (a) Category, K.; Tori, K.; Kimura, Y.; Yoshida, T.; Nagasaki, T.; Minato, H. J. Med. Chem. 1967, 10, 1147.
2. (b) Grollman, A. P. J. Biol. Chem. 1967, 242, 3226.
3. (c) Umezawa, H.; Aoyagi, T.; Morishima, H.; Matsuzaki, M.; Hamada, H.; Takeuchi, T. J. Antibiot. 1970, 23, 259.
4. (d) Molyneux, R. J.; James, L. F. Science 1982, 216, 190.
5. (e) Gruters, R. A.; Neefjes, J. J.; Tersmette, M.; de Goede, R. E. Y.; Tulp, A.; Huisman, H. G.; Miedema, F.; Ploegh, H. L. Nature 1987, 330, 74.
6. (f) Omura, S.; Fujimoto, T.; Otogurro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. Chem. 1991, 44, 113.
7. (g) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 11, 135.
8. (a) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049.
9. (b) Kang, S. H.; Jun, H.-S.; Youn, J.-H. Synlett 1998, 1045.
10. (c) Kang, S. H.; Choi, H.-w.; Kim, J. S.; Youn, J.-H. Chem. Commun. 2000, 227.
11. (a) Kang, S. H.; Ryu, D. H. Chem. Commun. 1996, 355.
12. (b) Kang, S. H.; Lee, S. B. Chem. Commun. 1998, 761.
13. (c) Kang, S. H.; Hwang, Y. S.; Youn, J.-H. Tetrahedron Lett. 2001, 42, 7599.
14. Hannun, Y. A.; Bell, R. M. Science 1989, 243, 500.
15. (a) Merrill, A. H.; Nimkar, S.; Menaldino, D.; Hannun, Y. A.; Loomis, C.; Bell, R. M.; Tyagi, S. R.; Lambeth, J. D.; Stevens, V. L.; Hunter, R.; Liotta, D. C. Biochemistry 1989, 28, 3138.
16. (b) Schwartz, G. K.; Jiang, J.; Kelsen, D.; Albino, A. P. J. Nat. Cancer Inst. 1993, 85, 402.
17. (a) Karlsson, K. A. In Biological Membranes; Chapman, D., Ed.; Academic Press: London, 1982; Vol. 4, p 1.
18. (b) Hakomori, S. In Handbook of Lipid Research, Vol. 3: Sphingolipid Biochemistry; Kanfer, J. M., Hakomori, S., Eds.; Plenum Press: New York, 1983; p 1.
19. (a) Hakomori, S. Ann. Rev. Biochem. 1981, 50, 733.
20. (b) Springer, T. A.; Lasky, L. A. Nature 1991, 349, 196.
21. (c) Oliveira, A.; Spiegel, S. Glycoconjugate J. 1992, 9, 110.
22. (d) Merrill, A. H., Jr.; Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins and Membranes; Vance, D. E.; Vance, J. E., Eds.; Elsevier Science: Amsterdam, 1996; p 309.
23. Naroti, T.; Morita, M.; Akimoto, K.; Koezuka, Y. Tetrahedron 1994, 50, 2771.
24. (a) Grag, H. S.; Sharma, M.; Bhakuni, D. S.; Pramanik, B. N.; Bose, A. K. Tetrahedron Lett. 1992, 33, 1641.
25. (b) Wong, C.-H.; Kamitakahara, H.; Suzuki, T.; Nichigori, N.; Suzuki, Y.; Kamie, O. Angew. Chem., Int. Ed. Engl. 1998, 37, 1524.
26. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nichijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908.
27. Marinier, A.; Martel, A.; Banville, J.; Bachand, C.; Remillard, R.; Lapointe, P.; Turmel, B.; Menard, M.; Harte Jr., W. E.; Kim Wright, J. J.; Todderud, G.; Tramposch, K. M.; Bajorath, J.; Hollenbaugh, D.; Aruffo, A. J. Med. Chem. 1997, 40, 3234.
28. Costantino, V.; Fattorusso, E.; Mangoni, A.; Rosa, M. D.; Ianaro, A. J. Am. Chem. Soc. 1997, 119, 12465.
29. Natori, T.; Morita, M.; Akimoto, K.; Koezuka, Y. Tetrahedron 1994, 50, 2771.
30. Higuchi, R.; Inukai, K.; Jhou, J. X.; Honda, M.; Komori, T.; Tsuji, S.; Nagai, Y. Liebigs Ann. Chem. 1993, 359.
31. Li, H.; Matsunaga, S.; Fusetani, N. Tetrahedron 1995, 51, 2273.
32. (a) Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075.
33. (b) Murakami, T.; Taguchi, K. Tetrahedron 1999, 55, 989.
34. (c) Chung, S.-K.; Lee, J.-M. Tetrahedron: Asymmetry 1999, 10, 1441.
35. (d) Hertweck, C.; Boland, W. J. Org. Chem. 1999, 64, 4426.
36. (e) Khiar, N.; Singh, K.; Garcia, M.; Martin-Lomas, M. Tetrahedron Lett. 1999, 40, 5779.
37. (f) Nakamura, T.; Shiozaki, M. Tetrahedron Lett. 1999, 40, 9063.
38. (g) Shirota, O.; Nakanishi, K.; Berova, N. Tetrahedron 1999, 55, 13643.
39. (h) Johnson, D. V.; Felfer, U.; Griengl, H. Tetrahedron 2000, 56, 781.
40. (i) Corey, E. J.; Choi, S. Tetrahedron Lett. 2000, 41, 2765.
41. (j) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538.
42. (k) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618.
43. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
44. Blackmore, P. R.; Cole, W. J.; Kociénski, P.J.; Morley, A. Synlett 1998, 26.
45. (a) Dondoni, A.; Perrone, D.; Turturici, E. J. Chem. Soc., Perkin Trans. 1 1997, 2389.
46. (b) Spanu, P.; Rassu, G.; Pinna, L.; Battistini, L.; Cariraghi, G. Tetrahedron: Asymmetry 1997, 19, 3237.
47. Tamura, M.; Kochi, J. Synthesis 1971, 305.
48. Li, Y.-L.; Mao, X.-H.; Wu, Y.-L. J. Chem. Soc. Perkin Trans. 1 1995, 1559.