A practical synthesis of D-erythro-sphingosine using a cross-metathesis approach

Organic and Biomolecular Chemistry

Volumn 2, Issue 11, 2004, Pages 1643-1646

  Torssell, Staffan ^a   Somfai, Peter ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CELL MEMBRANES; CHROMATOGRAPHY; DIMERIZATION; HYDROLYSIS; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL);

EPOXIDATION; METATHESIS; REGIOSELECTIVE OPENING;

AROMATIC HYDROCARBONS;

SPHINGOSINE; VINYL DERIVATIVE;

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

CATALYSIS; MOLECULAR STRUCTURE; SPHINGOSINE; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 2942752245     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b403568b     Document Type: Article

References (32)

1. K.-A. Karlsson, Trends Pharm. Sci., 1991, 12, 265.
2. Y. Hannun and R. M. Bell, Science, 1989, 243, 500.
3. Y. Hannun, Science, 1996, 274, 1855.
4. P. M. Koskinen and A. M. P. Koskinen, Synthesis, 1998, 1075.
5. J. M. Gargano and W. J. Lees, Tetrahedron Lett., 2001, 42, 5845.
6. T. Nakamura and M. Shiozaki, Tetrahedron. 2001, 57, 9087.
7. R. J. B. H. N. van der Berg, C. G. N. Korevaar, G. A. van der Marel, H. S. Overkleeft and J. H. van Boom, Tetrahedron Lett., 2002, 43, 8409.
8. J.-M. Lee, H.-S. Lim and S.-K. Chung, Tetrahedron: Asymmetry, 2002, 13, 343.
9. T. C. Nugent and T. Hudlicky, J. Org. Chem., 1998, 63, 510.
10. L. L. He, H. S. Byun and R. Bittman, J. Org. Chem., 2000, 65, 7627.
11. E. J. Corey and S. Choi, Tetrahedron Lett., 2000, 41, 2765.
12. B. Olofsson and P. Somfai, J. Org. Chem., 2003, 68, 2514.
13. S. J. Connon and S. Blechert, Angew. Chem., Int. Ed., 2003, 42, 1900.
14. A. Chatterjee, T.-L. Choi, D. P. Sanders and R. H. Grubbs, J. Am. Chem. Soc., 2003, 125, 11360.
15. 3) for comparison see refs. 16-18.
16. S. L. Schreiber, T. S. Schreiber and D. B. Smith, J. Am. Chem. Soc., 1987, 109, 1525.
17. V. Jäger, D. Schröter and B. Koppenhoefer, Tetrahedron, 1991, 47, 2195.
18. A. Romero and C.-H. Wong, J. Org. Chem., 2000, 65, 8264.
19. B. Olofsson, U. Khamrai and P. Somfai, Org. Lett., 2000, 2, 4087.
20. W. R. Roush and W. A. Adam, J. Org. Chem., 1985, 50, 3752.
21. V. Jäger, U. Stahl and W. Hummer, Synthesis, 1991, 776.
22. R. Martin, A. Moyano, M. A. Pericas and A. Riera, Org. Lett., 2000, 2, 93.
23. 2. This increased reactivity is not only an effect of increased reaction temperature. See: A. Fürstner, O. R. Thiel, L. Ackermann and H-J. Schanz and S. P. Nolan, J. Org. Chem., 2000, 65, 2204.
24. A. Fürstner and K. Langemann, J. Am. Chem. Soc., 1997, 119, 9130.
25. A. K. Ghosh, J. Cappiello and D. Shin, Tetrahedron Lett., 1998, 39, 4651.
26. S. Rodríguez, E. Castillo, M. Carda and J. A. Marco, Tetrahedron, 2002, 58, 1185.
27. 2 at rt for 15 min. The pure product was precipitated using pentane to give C (95%) as a green crystalline solid. See ref 28.
28. J. A. Love, J. P. Morgan, T. M. Trnks, and R. H. Grubbs, Angew. Chem., Int. Ed., 2002, 41, 4035.
29. B. Kang, D.-H. Kim, Y. Do and S. Chang, Org. Lett., 2003, 5, 3041.
30. T. Kanemitsu and P. H. Seeberger, Org. Lett., 2003, 5, 4541.
31. S. Katsumura, N. Yamamoto, E. Fukuda and S. Iwama, Chem. Lett., 1995, 393.
32. R. Julina, T. Herzig, B. Bernet and A. Vasella, Helv. Chim. Acta, 1986, 69, 368.