1-Deoxy-5-hydroxysphingolipids as new anticancer principles: An efficient procedure for stereoselective syntheses of 2-amino-3,5-diols

Organic Letters

Volumn 7, Issue 15, 2005, Pages 3155-3157

  Wiseman, John M ^a   McDonald, Frank E ^a   Liotta, Dennis C ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ANTINEOPLASTIC AGENT; GLYCOSPHINGOLIPID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; ANTINEOPLASTIC AGENTS; CATALYSIS; GLYCOSPHINGOLIPIDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 23044467762     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050829o     Document Type: Article

References (29)

1. Merrill, A. H., Jr.; Sandhoff, K. Sphingolipids: Metabolism and Cell Signaling. In Biochemistry of Lipids, Lipoprotein, and Membranes; Vance, D. E., Vance, J. E., Eds.; Elsevier: New York, 2002; pp 373-407.
2. (a) Hannun, Y. A.; Loomis, C. R.; Merrill, A. H., Jr.; Bell, R. M. J. Biol. Chem. 1986, 261, 12604.
3. (b) Smith, E. R.; Merrill, A. H.; Obeid, L, M.; Hannun, Y. A. Methods Enzymol. 2000, 312, 361.
4. (a) Obeid, L. M.; Linardic, C. M.; Karolak, L. A.; Hannun, Y. A. Science 1993, 259, 1769.
5. (b) Jan, M. S.; Liu, H. S.; Lin, Y. S. Biochem. Biophys. Res. Commun. 1999, 264, 724.
6. Symolon, H.; Schmelz, E. M.; Dillehay, D. L.; Merrill, A. H., Jr. J. Nutr. 2004, 134, 1157.
7. Spiegel, S.; Milstein, S. J. Biol. Chem. 2002, 277, 25851.
8. (a) Buehrer, B. M.; Bell, R. M. J. Biol. Chem. 1992, 267, 3154.
9. (b) Kedderis, L. B.; Bozigian, H. P.; Kleeman, J. M.; Hall, R. L.; Palmer, T. E.; Harrison, S. D. Fundam. Appl. Toxicol. 1995, 25, 201.
10. (c) Schwartz, G. K.; Ward, D.; Saltz, L.; Casper, E. S.; Speiss, T.; Mullen, E. Clin. Cancer Res. 1997, 3, 343.
11. Menaldino, D. S.; Bushnev, A.; Sun, A.; Liotta, D. C.; Symolon, H.; Desai, K.; Dillehay, D. L.; Peng, Q.; Wang, E.; Allegood, J.; Trotman-Pruett, S.; Sullards, M. C.; Merrill, A. H., Jr. Pharmacol. Res. 2003, 47, 373.
12. (a) Merrill, A. H. Jr.; Liotta, D. C.; Riley, R. T. Trends Cell Biol. 1996, 6, 218.
13. (b) Desai, K.; Sullards, M. C.; Allegood, J.; Wang, E.; Schmelz, E. M.; Hartl, M.; Humpf, H.-U.; Liotta, D. C.; Peng, Q.; Merrill, A. H., Jr. Biochim. Biophys. Acta 2002, 1585, 188.
14. (a) Shi, Y.; Peng, L. F.; Kishi, Y. J. Org. Chem. 1997, 62, 5666.
15. (b) Gurjar, M. K.; Rajendran, V.; Rao, B. V. Tetrahedron Lett. 1998, 39, 3803.
16. Myers, A. G.; Kung, D. W.; Zhong, B. J. Am. Chem. Soc. 2000, 122, 3236.
17. Nokami, J.; Ohga, M.; Nakamoto, H.; Matsubara, T.; Hussain, I.; Kataoka, K. J. Am. Chem. Soc. 2001, 123, 9168.
18. Determined by Mosher ester analysis (Supporting Information).
19. (a) Bartlett, P. A.; Meadows, J. D.; Brown, E. G.; Morimoto, A.; Jernstedt, K. K. J. Org. Chem. 1982, 47, 4013.
20. (b) Duan, J. J. W.; Smith, A. B. J. Org. Chem. 1993, 58, 3703.
21. (a) Wang, Y.-F.; Izawa, T.; Kobayashi, S.; Ohno, M. J. Am. Chem. Soc. 1982, 104, 6465.
22. (b) Davies, S. G.; Ichihara, O. Tetrahedron Lett. 1999, 40, 9313.
23. Ollivier, C.; Renaud, P. J. Am. Chem. Soc. 2001, 123, 4717.
24. (a) Shu, L.; Shi, Y. Tetrahedron 2001, 57, 5213.
25. (b) Shi, Y. Acc. Chem. Res. 2004, 37, 488.
26. The use of Oxone as the stoichiometric oxidant provided epoxycarbonate 13 with higher stereoselectivity (dr 19:1), but then two or three recycles with additional Shi chiral ketone catalyst 12 were generally required for complete conversion of substrates 9 and ent-9.
27. (a) McDonald, F. E.; Bravo, F.; Wang, X.; Wei, X.; Toganoh, M.; Rodriguez, J. R.; Do, B.; Neiwert, W. A.; Hardcastle, K. I. J. Org. Chem. 2002, 67, 2515.
28. (b) Valentine, J. C.; McDonald, F. E.; Neiwert, W. A.; Hardcastle, K. I. J. Am. Chem. Soc. 2005, 127, 4586.
29. In preparations of each diastereomer 14 and 18, trace amounts of the other diastereomer were isolated (arising from the minor enantiomers generated in either the crotyl transfer or epoxidation step) and were separated by silica gel chromatography, so that cyclization of each epoxy carbonate 13 and 17 afforded the major cyclic carbonates 14 and 18 respectively, in enantio- and diastereomerically pure form.