Versatile synthetic method for sphingolipids and functionalized sphingosine derivatives via olefin cross metathesis

Organic Letters

Volumn 8, Issue 24, 2006, Pages 5569-5572

  Yamamoto, Tetsuya ^a   Hasegawa, Hiroko ^a   Hakogi, Toshikazu ^a   Katsumura, Shigeo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINOALCOHOL; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; SERINE; SPHINGOLIPID; SPHINGOSINE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALKENES; AMINO ALCOHOLS; INDICATORS AND REAGENTS; SERINE; SPHINGOLIPIDS; SPHINGOSINE;

EID: 33846023340     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062258l     Document Type: Article

References (25)

1. For recent reviews on signal transduction mediated by sphingolipids, see: (a) Sphingolipid Metabolism and Signaling Minireview Series;
2. Smith, W. L., Merrill, A. H., Jr., Eds.; J. Biol. Chem. 2002, 277, 25841.
3. (b) Cremesti, A. E.; Goni, F. M.; Kolesnick, R. FEBS Lett. 2002, 531, 47 and references therein.
4. (a) Suzuki, A.; Igarashi, Y. Protein Nucleic Acid Enzyme 2002, 47, 315.
5. (b) Simons, K.; Ikonen, E. Science 2000, 290, 1721.
6. (c) Simons, K.; Ikonen, K. Nature 1997, 387, 569 and references therein.
7. (a) Hakogi, T.; Monden, Y.; Taichi, M.; Iwama, S.; Fujii, S.; Ikeda, K.; Katsumura, S. J. Org. Chem. 2002, 67, 4839.
8. (b) Hakogi, T.; Taichi, M.; Katsumura, S. Org. Lett. 2003, 5, 2801.
9. (c) Hasegawa, H.; Yamamoto, T.; Hatano, S.; Hakogi, T.; Katsumura, S. Chem. Lett. 2004, 33, 1592.
10. (d) Hakogi, T.; Fujii, S.; Morita, M.; Ikeda, K.; Katsumura, S. Bioorg. Med. Chem. Lett. 2005, 15, 2141.
11. (e) Hakogi, T.; Yamamoto, T.; Fujii, S.; Ikeda, K.; Katsumura, S. Tetrahedron Lett. 2006, 47 2627.
12. Hakogi, T.; Shigenari, T.; Katsumura, S.; Sano, T.; Kohno, T.; Igarashi, Y. Bioorg. Med. Chem. Lett. 2003, 13, 661.
13. Shigenari, T.; Hakogi, T.; Katsumura, S. Chem. Lett. 2004, 33, 594.
14. (a) Grubbs, R. H. Handbook of Metathesis; Wiley-VCH: Germany, 2003.
15. (b) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900 and references therein.
16. Katsumura, S.; Kondo, A.; Han, Q. Chem. Lett. 1991, 1, 1245.
17. Torssell, S.; Somfai, P. Org. Biomol. Chem. 2004, 2, 1643.
18. Rai, A. N.; Basu, A. Org. Lett. 2004, 6, 2861.
19. So, R. C.; Ndonye, R.; Izmirian, D. P.; Richardson, S. K.; Guerrera, R. L.; Howell, A. R. J. Org. Chem. 2004, 69, 3233.
20. (a) Murakami, M.; Iwama, S.; Fujii, S.; Ikeda, K.; Katsumura, S. Bioorg. Med. Chem. Lett. 1997, 7, 1725.
21. (b) Iguchi, S.; Nakai, H.; Hayashi, M.; Yamamoto, H. J. Org. Chem. 1979, 44, 1363.
22. Hofmann, R. V.; Maslouh, N. Lee, F.-C. J. Org. Chem. 2002, 67, 1045.
23. (a) Szulc, Z. M.; Hannun, Y. A.; Bielawska, A. Tetrahedron Lett. 2000, 41, 7821.
24. (b) Oza, V. B.; Corcoran, R. C. J. Org. Chem. 1995, 60, 3680.
25. 1H NMR.