A Four-Step Diastereoselective Synthesis of d-erythro-Sphingosine by an Enantioselective Aldol Reaction Using a Titanium Enolate Derived from a Chiral Iminoglycinate

Journal of Organic Chemistry

Volumn 59, Issue 11, 1994, Pages 3240-3242

  Solladié Cavallo, Arlette ^a   Koessler, Jean L ^a  

^a EHICS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

SPHINGOSINE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0028364176     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00090a052     Document Type: Article

References (28)

1. Feizi, T. Nature 1985, 314, 52.
2. Devant, R. M. Kontakte (Merck) 1993, 3, 11-28.
3. Reist, E. J.; Chistie, P. H. J. Org. Chem. 1970, 35, 3521.
4. Gigg, R.; Conant, R. J. Chem. Soc., Perkin Trans. I 1977, 2006.
5. Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481.
6. Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393.
7. Boutin, R. H.; Rapoport, H. J. Org. Chem. 1986, 51, 5320.
8. Radung, H. E.; Devant, R. M.; Eiermann, V. Liebigs Ann. Chem. 1988, 1103.
9. Herold, P. Helv. Chim. Acta 1988, 71, 354.
10. Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1986, 69, 368.
11. Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1988, 29, 239.
12. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, pp 305-310.
13. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832.
14. Duthaler, R. O. Helv. Chim. Acta 1990, 73, 659.
15. El Achgar, A.; Boumzebra, M.; Roumestant, M. L.; Viallefont, P. Tetrahedron 1988, 44, 5319.
16. Groth, U.; Schöllkopf, U.; Tiller, T. Tetrahedron 1991, 47, 2835.
17. Seebach, D.; Hungerbühler, E.; Naef, R.; Schnurrenberger, P.; Weismann, B.; Züger, M. Synthesis 1982, 138.
18. Harisson, C. Tetrahedron Lett. 1987, 28, 4135.
19. Annunziata, R.; Cinquini, M.; Cozzi, F.; Cozzi, P. G.; Consolandi, E. Tetrahedron 1991, 47, 7897-7910.
20. Oguri, T.; Kaway, N.; Yamada, S. Chem. Pharm. Bull. Jpn. 1978, 26, 803.
21. Solladié-Cavallo, A.; Simon, M. C. Tetrahedron Lett, 1989, 30, 6011.
22. Solladié-Cavallo, A.; Simon-Wermeister, M. C.; Schwarz, J. Organometallics 1993, 12, 3743.
23. Carlson, R. G.; Pierce, J. K. J. Org. Chem. 1971, 36, 2319.
24. Solladié-Cavallo, A.; Simon, M. C.; Fischer, J.; DeCian, A. Bull. Soc. Chim. Fr. 1989, 4, 544-548.
25. Seki, H.; Koga, K.; Matsuo, H.; Ohki, S.; Matsuo, I.; Yamada, S. I. Chem. Pharm. Bull. 1965, 13, 995.
26. Stoffel, W.; Zierenberg, O.; Tunggal, B. D. Hoppe-Seyler's Z. Physiol. Chem. 1972, 354, 1962.
27. Bold, G.; Duthaler, R. O.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 497.
28. Holloway, H. Chem. Ind. 1962, Feb. 3, 214.