Enantioselective Synthesis of 3-Deoxy-(R)-sphingomyelin from (S)-1-(4′-Methoxyphenyl)glycerol

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2560-2563

  Byun, Hoe Sup ^a   Sadlofsky, Jason A ^a   Bittman, Robert ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001200273     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971977y     Document Type: Article

References (19)

1. For recent reviews, see: (a) Spiegel, S.; Merrill, A. H., Jr. FASEB J. 1996, 10, 1388-1397. (b) Hannun, Y. Science 1996, 274, 1855-1859. (c) Spiegel, S.; Foster, D.; Kolesnick, R. N. Curr. Opin. Cell Biol. 1996, 8, 159-167. (d) Merrill, A. H., Jr.; Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins, and Membranes, 2nd ed.; Vance, D. E., Vance, J., Eds.; Elsevier: Amsterdam, 1996; Vol. 31, pp 309-338. (e) Ghosh, S.; Strum, J. C.; Bell, R. M. FASEB J. 1997, 11, 45-50.
2. For recent reviews, see: (a) Spiegel, S.; Merrill, A. H., Jr. FASEB J. 1996, 10, 1388-1397. (b) Hannun, Y. Science 1996, 274, 1855-1859. (c) Spiegel, S.; Foster, D.; Kolesnick, R. N. Curr. Opin. Cell Biol. 1996, 8, 159-167. (d) Merrill, A. H., Jr.; Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins, and Membranes, 2nd ed.; Vance, D. E., Vance, J., Eds.; Elsevier: Amsterdam, 1996; Vol. 31, pp 309-338. (e) Ghosh, S.; Strum, J. C.; Bell, R. M. FASEB J. 1997, 11, 45-50.
3. For recent reviews, see: (a) Spiegel, S.; Merrill, A. H., Jr. FASEB J. 1996, 10, 1388-1397. (b) Hannun, Y. Science 1996, 274, 1855-1859. (c) Spiegel, S.; Foster, D.; Kolesnick, R. N. Curr. Opin. Cell Biol. 1996, 8, 159-167. (d) Merrill, A. H., Jr.; Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins, and Membranes, 2nd ed.; Vance, D. E., Vance, J., Eds.; Elsevier: Amsterdam, 1996; Vol. 31, pp 309-338. (e) Ghosh, S.; Strum, J. C.; Bell, R. M. FASEB J. 1997, 11, 45-50.
4. For recent reviews, see: (a) Spiegel, S.; Merrill, A. H., Jr. FASEB J. 1996, 10, 1388-1397. (b) Hannun, Y. Science 1996, 274, 1855-1859. (c) Spiegel, S.; Foster, D.; Kolesnick, R. N. Curr. Opin. Cell Biol. 1996, 8, 159-167. (d) Merrill, A. H., Jr.; Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins, and Membranes, 2nd ed.; Vance, D. E., Vance, J., Eds.; Elsevier: Amsterdam, 1996; Vol. 31, pp 309-338. (e) Ghosh, S.; Strum, J. C.; Bell, R. M. FASEB J. 1997, 11, 45-50.
5. For recent reviews, see: (a) Spiegel, S.; Merrill, A. H., Jr. FASEB J. 1996, 10, 1388-1397. (b) Hannun, Y. Science 1996, 274, 1855-1859. (c) Spiegel, S.; Foster, D.; Kolesnick, R. N. Curr. Opin. Cell Biol. 1996, 8, 159-167. (d) Merrill, A. H., Jr.; Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins, and Membranes, 2nd ed.; Vance, D. E., Vance, J., Eds.; Elsevier: Amsterdam, 1996; Vol. 31, pp 309-338. (e) Ghosh, S.; Strum, J. C.; Bell, R. M. FASEB J. 1997, 11, 45-50.
6. For a review, see: Byun, H.-S.; Bittman, R. In Phospholipids Handbook; Cevc, G., Ed.; Marcel Dekker: New York, 1993; pp 97-140.
7. Kan, C.-C.; Ruan, Z.-S.; Bittman, R. Biochemistry 1991, 30, 7759-7766.
8. Lister, M. D.; Ruan, Z.-S.; Bittman, R. Biochim. Biophys. Acta 1995, 1256, 25-30.
9. Grönberg, L.; Ruan, Z.-S.; Bittman, R.; Slotte, J. P. Biochemistry 1991, 30, 10746-10754.
10. For a review, see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
11. Byun, H.-S.; Kumar, E. R.; Bittman, R. J. Org. Chem. 1994, 59, 2630-2633.
12. Takano, S.; Seya, K.; Goto, E.; Hirama, M.; Ogasawara, K. Synthesis 1983, 116-117.
13. Takano, S.; Moriya, M.; Suzuki, M.; Iwabuchi, Y.; Sugihara, T.; Ogasawara, K. Heterocycles 1990, 31, 1555-1562.
14. (a) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538-7539.
15. (b) For a review, see: Lohary, B. B. Synthesis 1992, 1035-1052.
16. Byun, H.-S.; Bittman, R. J. Org. Chem. 1996, 61, 8706-8708.
17. For a review of Birch reductions of aromatic compounds, see: Rabideau, P. W.; Marcinow, Z. Org. React. 1992, 42, 1-334.
18. Erukulla, R. K.; Byun, H.-S.; Bittman, R. Tetrahedron Lett. 1994, 35, 5783-5784.
19. Takano, S.; Setoh, M.; Ogasawara, K. Heterocycles 1992, 34, 173-180.