Sphingosine, an enigmatic lipid: A review of recent literature syntheses

Synthesis

Volumn , Issue 8, 1998, Pages 1075-1091

  Koskinen, Päivi M ^a   Koskinen, Ari M P ^a  

^a UNIVERSITY OF OULU   (Finland)

Author keywords

Sphingosine; Total synthesis

Indexed keywords

SPHINGOLIPID; SPHINGOSINE;

DRUG SYNTHESIS; EUKARYOTIC CELL; HUMAN; MEMBRANE COMPONENT; PEPTIDE SYNTHESIS; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 0031873509     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-4494     Document Type: Review

References (125)

1. a) Will, R.G.; Ironside, J.M.; Zeidler, M.; Cousens, S.N.; Estibeiro, K.; Alperovitch, A.; Poser, S.; Pocchiari, M.; Hofman, A.; Smith, P.G. Lancet 1996, 347, 921.
2. b) Collinge, J.; Sidle, K.C.L.; Meads, J.; Ironside, J.; Hill, A.F. Science 1996, 383, 685.
3. Hill, A.F.; Desbruslais, M.; Joiner, S.; Sidle, K.C.L.; Gowland, I.; Collinge, J. Nature 1997, 389, 448.
4. Bruce, M.E.; Will, R.G.; Ironside, J.W.; McConnell, I.; Drummond, D.; Suttie, A.; McCardle, L.; Chree, A.; Hope, J.; Birkett, C.; Cousens, S.; Fraser, H.; Bostock, C.J. Nature 1997, 389, 498.
5. Kirschner, E.M. Chem. Eng. News 1997, March 3, p 19.
6. Thudichum, J.L.W. A Treatise on the Chemical Constitution of the Brain 1884, Lontoo: Bailliere. New edition 1962, Archon Books, Hamden, Connecticut, USA.
7. Devant, R.M. Kontakte 1992, 11.
8. Hakomori, S. J. Biol. Chem. 1990, 265, 18713.
9. Van Meer, G.; Burger, K.N.J. Trends in Cell Biology 1992, 2, 332.
10. Karlsson, K.-A. Lipids 1970, 5, 878.
11. Kanfer, J.N.; Hakomori, S. Handbook of Lipid Research, Vol. 3 Sphingolipid Biochemistry; Hanahan, D.J., Ed; Plenum Press: New York, 1983.
12. Advances in Lipid Research: Sphingolipids and Their Metabolites, Vol. 25 & 26; Bell, R.M.; Hannun, Y.A.; Merrill, Jr. A.H., Eds.; Academic Press: Orlando FL, 1993.
13. Lee, J.Y.; Hannun, Y.A.; Obeid, L.M. J. Biol. Chem. 1996, 271, 13169.
14. Hannun, Y.A. J. Biol. Chem. 1994, 269, 3125.
15. a) Gómez-Muñoz, A.; Waggoner, D.W.; O'Brien, L.; Brindley, D.N. J. Biol. Chem. 1995, 270, 26318.
16. b) Merrill, Jr., A.H. Nutr. Rev. 1992, 50, 78.
17. a) Merrill, Jr., A.H.; Schmelz, E.-M.; Dillehay, D.L.; Spiegel, S.; Shayman, J.A.; Schroeder, J.J.; Riley, R.T.; Voss, K.A.; Wang, E. Toxicol. Appl. Pharmacol. 1997, 142, 208.
18. b) Merrill, Jr., A.H. J. Bioenerg. Biomembr. 1991, 23, 83.
19. a) Levene, P.A.; West, C.J. J. Biol. Chem. 1913, 16, 549.
20. b) Levene, P.A.; West, C.J. J. Biol. Chem. 1914, 18, 481.
21. Klenk, E. Z. Physiol. Chem. 1929, 185, 169.
22. a) Carter, H.E.; Glick, F.J.; Norris, W.P.; Phillips, G.E. J. Biol. Chem. 1947, 170, 285.
23. b) Carter, H.E.; Glick, F.J.; Norris, W.P.; Phillips, G.E. J. Biol. Chem. 1942, 142, 449.
24. a) Carter, H.E.; Humiston, C.G. J. Biol. Chem. 1951, 191, 727.
25. b) Kiss, J.; Fodor, G.; Banfii, D. Helv. Chim. Acta 1954, 37, 1471.
26. Klenk, E.; Faillard, H. Z. physiol. Chem. 1955, 299, 48.
27. Carter, H.E.; Shapiro, D.; Harrison, J.B. J. Am. Chem. Soc. 1953, 75, 1007.
28. e) Carter, H.E.; Shapiro, D. J. Am. Chem. Soc. 1953, 75, 5131.
29. Mislow, K. J. Am. Chem. Soc. 1952, 74, 5155.
30. Marinetti, G.; Stotz, E. J. Am. Chem. Soc. 1954, 76, 1347.
31. Shapiro, D.; Segal, H.; J. Am. Chem. Soc. 1954, 76, 5894.
32. Shapiro, D.; Segal, H.; Flowers, H.M. J. Am. Chem. Soc. 1958, 80, 1194.
33. Grob, C.A.; Gadient, F. Helv. Chim. Acta 1957, 40, 1145.
34. Reist, E.J.; Christie, P.H. J. Org. Chem. 1970, 35, 4127.
35. Gigg, J.; Gigg, R.; Warren, C.D. J. Chem. Soc. 1966, 1872.
36. Reist, E.J.; Christie, P.H. J. Org. Chem. 1970, 35, 3521.
37. a) Gigg, R.; Conant, R. J. Chem. Soc., Perkin Trans 1 1977, 2006.
38. b) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101.
39. Schmidt, R.R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481.
40. Zimmermann, P.; Schmidt, R.R. Liebigs. Ann. Chem. 1988, 663.
41. e) Ohashi, K.; Yamagiwa, Y.; Kamikawa, T.; Kates, M. Tetrahedron Lett. 1988, 29, 1185.
42. f) Sugawara, T.; Narisada, M. Carbohydr. Res. 1989, 194, 125.
43. g) Hirata, N.; Yamagiwa, Y.; Kamikawa, T. J. Chem. Soc., Perkin Trans 1 1991, 2279.
44. a) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491.
45. b) Roush, W.R.; Adam, M.A. J. Org. Chem. 1985, 50, 3752.
46. Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1986, 69, 368.
47. Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205.
48. e) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820.
49. a) Schmidt, R.R.; Kläger, R. Angew. Chem. 1982, 94, 215;
50. Angew. Chem., Int. Ed. Engl. 1982, 21, 210.
51. b) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1988, 29, 239.
52. Nicolaou, K.C.; Caulfield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910.
53. a) Newman, H. J. Am. Chem. Soc. 1973, 95, 4096.
54. b) Tkaczuk, P.; Thornton, E.R. J. Org. Chem. 1981, 46, 4393.
55. Mori, K.; Funaki, Y. Tetrahedron 1985, 41, 2379.
56. Boutin, R.H.; Rapoport, H. J. Org. Chem. 1986, 51, 5320.
57. e) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A. J. Chem. Soc., Chem. Commun. 1988, 10.
58. f) Nimkar, S.; Menaldino, D.; Merrill, A.H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037.
59. g) Garner, P.; Park, J.M.; Malecki, E. J. Org. Chem. 1988, 53, 4395.
60. h) Radunz, H.E.; Devant, R.M.; Eiermann, V. Liebigs Ann. Chem. 1988, 1103.
61. Herold, P. Helv. Chim. Acta 1988, 71, 354.
62. j) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439.
63. Polt, R.; Peterson, M.A. Tetrahedron Lett. 1990, 31, 4985.
64. Koskinen, A.M.P. Asymmetric Synthesis of Natural Products; Wiley: Chichester, 1993, p 81.
65. a) Garner, P. Tetrahedron Lett. 1984, 25, 5855.
66. b) Garner, P.; Ramakanth, S. J. Org. Chem. 1986, 51, 2609.
67. Garner, P.; Park, J.M. J. Org. Chem. 1987, 52, 2361.
68. Yamanoi, T.; Akiyama, T.; Ishida, E.; Abe, H.; Amemiya, M.; Inazu, T. Chem. Lett. 1989, 335.
69. a) Garigipati, R.S.; Weinreb, S.M. J. Am. Chem. Soc. 1983, 105, 4499.
70. b) Garigipati, R.S.; Freyer, A.J.; Whittle, R.R.; Weinreb, S.M. J. Am. Chem. Soc. 1984, 106, 7861.
71. a) Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. Chem. Soc., Perkin Trans. 1 1986, 1339.
72. b)Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. Chem. Soc., Perkin Trans. ibid. 1986, 1345.
73. Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917.
74. Hino, T.; Nakakyama, K.; Taniguchi, M.; Nakagawa, M. J. Chem. Soc., Perkin Trans 1 1986, 1687.
75. Findeis, M.A.; Whitesides, G.M. J. Org. Chem. 1987, 52, 2838.
76. Groth, U.; Schöllkopf, U.; Tiller, T. Tetrahedron 1991, 47, 2835.
77. Funk, R.L.; Bolton, G.L. J. Am. Chem. Soc. 1988, 110, 1290.
78. Polt, R.; Peterson, M.A.; DeYoung, L. J. Org. Chem. 1992, 57, 5469.
79. a) O'Donnell, M.J.; Polt, R.L. J. Org. Chem. 1982, 47, 2663.
80. b) O'Donnell, M.J.; Bennett, W.D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353.
81. Yadav, J.S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191.
82. Yadav, J.S.; Chandler, M.C.; Bhalchandra, V.J. Tetrahedron Lett. 1988, 29, 2737.
83. Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645.
84. Schlosser von, M.; Christmann, K.F. Angew. Chem. 1965, 77, 682;
85. Angew. Chem., Int. Ed. Engl. 1965, 4, 689.
86. Wild, R.; Schmidt, R.R. Tetrahedron: Asymmetry 1994, 5, 2195.
87. Evans, D. A.; Hoveyda, A.H. J. Am. Chem. Soc. 1990, 112, 6447.
88. Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240.
89. a) Dutthaler, R.O.; Hafner, A. Chem. Rev. 1992, 92, 807.
90. b) Bold, G.; Dutthaler, R.O.; Riediker, M. Angew. Chem. 1989, 101, 491;
91. Angew. Chem., Int. Ed. Engl. 1989, 28, 497.
92. Hudlicky, T.; Nugent, T.; Griffith, W. J. Org. Chem. 1994, 59, 7944.
93. Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745.
94. Murakami, T.; Minamikawa, H.; Hato, M. J. Chem. Soc., Perkin. Trans. 1 1992, 1875.
95. a) Corey, E.J.; Clark, D.A.; Goto, G.; Marfat, A.; Mioskowski, C.; Samuelsson, B.; Hammarström, S. J. Am. Chem. Soc. 1980, 102, 1436.
96. b) Rollin, P.; Pougny, J.-R. Tetrahedron 1986, 42, 3479.
97. Cornforth, J.W.; Cornforth, R.H.; Mathew, K.K. J. Chem. Soc. 1959, 112.
98. Crabbé, P.; Guzmán, A. Tetrahedron Lett. 1972, 113, 115.
99. Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans 1 1996, 823.
100. Kobayashi, S.; Hayashi, T.; Kawasuji, T. Tetrahedron Lett. 1994, 35, 9573.
101. Katsumura, S.; Kondo, A.; Han, Q. Chem. Lett. 1991, 1245.
102. Katsumura, S.; Yamamoto, N.; Fukuda, E.; Iwama, S. Chem. Lett. 1995, 393.
103. Enders, D.; Whitehouse, D.L.; Runsink, J. Chem. Eur. J. 1995, 1, 382.
104. a) Remion, J.; Dumont, W.; Krief, A. Tetrahedron Lett. 1976, 17, 1385.
105. b) Léonard-Coppens, A.M.; Krief, A. Tetrahedron Lett. 1976, 17, 3227.
106. Remion, J.; Krief, A. Tetrahedron Lett. 1976, 17, 3743.
107. Clive, D.L.J.; Kale, V.N. J. Org. Chem. 1981, 46, 231.
108. e) Reich, H.J.; Chow, F. J. Chem. Soc., Chem. Commun. 1975, 790.
109. Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927.
110. a) Davis, F.A.; Zhou, P. Tetrahedron Lett. 1994, 35, 7525.
111. b) Davis, F.A.; Reddy, G.V.; Liu, H. J. Am. Chem. Soc. 1995, 117, 3651.
112. Davis, F.A.; Reddy, G.V. Tetrahedron Lett. 1996, 37, 4349.
113. Tuch, A.; Sanière, M.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron: Asymmetry 1996, 7, 897.
114. Miyata, O.; Yamaguchi, S.; Ninomiya, I.; Naito, T.; Okamura, K. Chem. Pharm. Bull. 1996, 44, 636.
115. Corey, E.J.; Ensley, H.E. J. Am. Chem. Soc. 1975, 97, 6908.
116. Bettelli, E.; Chinzari, P.; D'Andrea, P.; Passacantilli, P.; Piancatelli, G.; Topai, A. Korean J. Med. Chem. 1996, 6, 339;
117. Chem. Abstr. 1997, 126, 157 730.
118. Passacantilli, P. Tetrahedron Lett. 1989, 30, 5349.
119. Li, Y.-L.; Wu, Y.-L. Liebigs Ann. Chem. 1996, 12, 2079.
120. Koskinen, A.M.P.; Koskinen, P.M. Methods in Enzymology: Sphingolipid metabolism and cell signaling; Merrill, Jr, A.H.; Hannun, Y.A., Eds.; manuscript invited for publication.
121. Koskinen, A.M.P.; Krische, M.J. Synlett 1990, 665.
122. Koskinen, A.M.P.; Koskinen, P.M. Synlett 1993, 501.
123. Koskinen, A.M.P.; Koskinen, P.M. Tetrahedron Lett. 1993, 34, 6765.
124. Koskinen, A.M.P.; Koskinen, P.M. US Pat. No. 5 426 228 (1995); Chem. Abstr. 1995, 123, 170 072.
125. Beilstein, Vol. IV, Supplement III 1962, 854.