Aziridine-2-carboxylic acid mediated asymmetric synthesis of D-erythro-and L-threo-sphingosine from a common precursor

Tetrahedron Letters

Volumn 37, Issue 25, 1996, Pages 4349-4352

  Davis, Franklin A ^a   Reddy, G Venkat ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; SPHINGOSINE DERIVATIVE;

ARTICLE; DRUG ACETYLATION; DRUG HYDROLYSIS; DRUG SYNTHESIS; ENANTIOMER; PRECURSOR; REDUCTION; STEREOCHEMISTRY;

EID: 0029883037     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00827-1     Document Type: Article

References (27)

1. For a review on optically active aziridines see: Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
2. For leading references to optically active aziridine 2-carboxylic acids see: Davis, F. A.; Zhou, P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243.
3. Davis, F. A.; Zhou, P. Tetrahedron Lett. 1994, 35, 7525.
4. Kanfer, J. N.; Hakomori, S. Sphingolipid Biochemistry, Plenum Press: New York 1983. Radin, N. S.; Shayman, J. A.; Inokuchi, J. Avd. Lipid Res., 1993, 26, 183.
5. Kanfer, J. N.; Hakomori, S. Sphingolipid Biochemistry, Plenum Press: New York 1983. Radin, N. S.; Shayman, J. A.; Inokuchi, J. Avd. Lipid Res., 1993, 26, 183.
6. Springer, T. A.; Lasky, L. A. Nature 1991, 349, 196. Feizi, T. Trends Biochem. Sci. 1991, 16, 84. Karlsson, K.-A. Trends Pharm. Sci. 1991, 12, 265.
7. Springer, T. A.; Lasky, L. A. Nature 1991, 349, 196. Feizi, T. Trends Biochem. Sci. 1991, 16, 84. Karlsson, K.-A. Trends Pharm. Sci. 1991, 12, 265.
8. Springer, T. A.; Lasky, L. A. Nature 1991, 349, 196. Feizi, T. Trends Biochem. Sci. 1991, 16, 84. Karlsson, K.-A. Trends Pharm. Sci. 1991, 12, 265.
9. Harouse, J. M.; Bhat, S.; Spitalnik, S. L.; Laughlin, M.; Stefano, K.; Silberberg, D. H.; Gonzalez-Scarano, F. Science 1991, 253, 320.
10. Merrill, A. H. Jr.; Nimkar, S.; Menaldino, D.; Hannun, Y. A.; Loomis, C.; Bell, R. M.; Tyahi, S. R.; Lambeth, J. D.; Stevens, V. L.; Hunter, R.; Liotta, D. C. Biochemistry, 1989, 28, 3138.
11. Zhang, H.; Buckley, N. E.; Gibson, K.; Spiegel, S.; J. Biol. Chem. 1990, 265, 76. Olivera, A.; Spiegel, S. Glyococonjugate J. 1992, 9, 110.
12. Zhang, H.; Buckley, N. E.; Gibson, K.; Spiegel, S.; J. Biol. Chem. 1990, 265, 76. Olivera, A.; Spiegel, S. Glyococonjugate J. 1992, 9, 110.
13. 11 its saturated analog, have been prepared from trans-aziridine 2-methanols with varying degrees of success.
14. Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917.
15. Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. C. S. Perkin Trans I, 1986, 1339. Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. C. S. Perkin Trans I, 1986, 1345.
16. Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. C. S. Perkin Trans I, 1986, 1339. Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. C. S. Perkin Trans I, 1986, 1345.
17. For leading references to the asymmetric synthesis of sphingosine see: (a) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382.
18. (b) Hudlicky, T.; Nugent, T.; Griffith, W. J. Org. Chem. 1994, 59, 7944.
19. (c) Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037.
20. Davis, F. A.; Reddy, G. V.; Liu, H. J. Am. Chem. Soc. 1995, 117, 3651.
21. For recent examples of the Pummerer rearrangement using TFAA see: Jung, M. E.; Kim, C.; von dem Bussche, L. J. Org. Chem. 1994, 59, 3248. Page, P. C. B.; Shuttleworth, S. J.; McKenzie, M. J.; Schilling, M. B.; Tapolczay, D. J. Synthesis, 1995, 73. Bueno, A. B.; Carreno, M. C.; Garcia Ruano, J. L.; Rubio, A. Tetrahedron: Asymmetry 1992, 3, 251.
22. For recent examples of the Pummerer rearrangement using TFAA see: Jung, M. E.; Kim, C.; von dem Bussche, L. J. Org. Chem. 1994, 59, 3248. Page, P. C. B.; Shuttleworth, S. J.; McKenzie, M. J.; Schilling, M. B.; Tapolczay, D. J. Synthesis, 1995, 73. Bueno, A. B.; Carreno, M. C.; Garcia Ruano, J. L.; Rubio, A. Tetrahedron: Asymmetry 1992, 3, 251.
23. For recent examples of the Pummerer rearrangement using TFAA see: Jung, M. E.; Kim, C.; von dem Bussche, L. J. Org. Chem. 1994, 59, 3248. Page, P. C. B.; Shuttleworth, S. J.; McKenzie, M. J.; Schilling, M. B.; Tapolczay, D. J. Synthesis, 1995, 73. Bueno, A. B.; Carreno, M. C.; Garcia Ruano, J. L.; Rubio, A. Tetrahedron: Asymmetry 1992, 3, 251.
24. Newman, H. J. Org. Chem. 1965, 30, 1287. Franck, B.; Lubs, H. J. Angew. Chem., Int. Ed. Engl. 1968, 7, 223. Imazawa, M.; Eckstein, F. J. Org. Chem. 1979, 44, 2039.
25. Newman, H. J. Org. Chem. 1965, 30, 1287. Franck, B.; Lubs, H. J. Angew. Chem., Int. Ed. Engl. 1968, 7, 223. Imazawa, M.; Eckstein, F. J. Org. Chem. 1979, 44, 2039.
26. Newman, H. J. Org. Chem. 1965, 30, 1287. Franck, B.; Lubs, H. J. Angew. Chem., Int. Ed. Engl. 1968, 7, 223. Imazawa, M.; Eckstein, F. J. Org. Chem. 1979, 44, 2039.
27. See Solladie-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240.