Synthesis of d/l-erythro-Sphingosine Using a Tethered
Aminohydroxylation Reaction as the Key Step

José Antonio Morales-Serna; Yolanda Díaz; M. Isabel Matheu; Sergio Castillón

doi:10.1055/s-0028-1083367

SHORTPAPER

Synthesis of d/l-erythro-Sphingosine Using a Tethered Aminohydroxylation Reaction as the Key Step

José Antonio Morales-Serna, Yolanda Díaz, M. Isabel Matheu, Sergio Castillón*
Departamento de Química Analítica y Química Orgánica, Universitat Rovira I Virgili, C/Marcel.li Domingo s/n, 43007 Tarragona, Spain
Fax: +34(977)558446; e-Mail: sergio.castillon@urv.net;

Abstract

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Abstract

A diastereoselective synthesis of racemic d/l-erythro-sphingosine is described. The approach involves employing tethered aminohydroxylation (TA) to introduce the 2-amino and 3-hydroxy functions with required stereochemistry.

Key words

sphingolipids - sphingosine - ceramide - amino alcohols - diasteroselectivity

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References

1 Thudichum JLW. A Treatise on the Chemical Constitution of the Brain Bailliere, Tindall and Cox; London: 1884.

2 Tani M. Ito M. Igarashi Y. Cell. Signal. 2007, 19: 229

3 Riethmüller J. Riehle A. Grassmé H. Gulbins E. Biochim. Biophys. Acta 2006, 1758: 2139

4 Snook CF. Jones JA. Hannun YA. Biochim. Biophys. Acta 2006, 1761: 927

5 El Alwani M. Wu BX. Obeid LM. Hannun YA. Pharmacol. Ther. 2006, 112: 171

6 Argraves KM. Wilkerson BA. Argraves WS. Fleming PA. Obeid LM. Drake CJ. J. Biol. Chem. 2004, 279: 50580

7 Heung LJ. Luberto Ch. Del Poeta M. Infect. Immun. 2006, 74: 28

8 Summers SA. Nelson DH. Diabetes 2005, 54: 591

9 Modrak DE. Gold DV. Goldenberg DM. Mol. Cancer. Ther. 2006, 5: 200

10 Zhou S. Zhou H. Walian PJ. Jap BK. Biochemistry 2007, 46: 2553

11 Kolter T. Sandhoff K. Biochim. Biophys. Acta 2006, 1758: 2057

12 Merril AH. Nimkar S. Menaldino D. Hannun YA. Loomis C. Bell RM. Tyahi SR. Lambeth JD. Stevens VL. Hunter R. Liotta DC. Biochemistry 1989, 28: 3138

13 Sachs CW. Ballas LM. Mascarella SW. Safa AR. Lewin AH. Loomis C. Carroll FI. Bell RM. Fine RL. Biochem. Pharmacol. 1996, 52: 603

For reviews, see:

14a Merrill AH. Hannun YA. Methods Enzymol. 2000, 311: 91

14b Koskinen PM. Koskinen AMP. Synthesis 1998, 1075

14c Liao J. Tao J. Lin G. Liu D. Tetrahedron 2005, 61: 4715

15 Garigipati RS. Freyer AJ. Whittle RR. Weinreb SM. J. Am. Chem. Soc. 1984, 106: 7861

16a Li G. Chang H.-T. Sharpless KB. Angew. Chem., Int. Ed. Engl. 1996, 35: 451

16b For a review, see: Bodkin JA. McLeod MD. J. Chem. Soc., Perkin Trans. 1 2002, 2733

17a Donohoe TJ. Helliwell M. Johnson PD. Keenan M. Chem. Commun. 2001, 2078

17b Donohoe TJ. Cowley A. Johnson PD. Keenan M. J. Am. Chem. Soc. 2002, 124: 12934

17c Donohoe TJ. Johnson PD. Pye RJ. Org. Biomol. Chem. 2003, 1: 2025

17d Donohoe TJ. Johnson PD. Keenan M. Pye RJ. Org. Lett. 2004, 6: 2583

17e Donohoe TJ. Chughtai MJ. Klauber DJ. Griffin D. Campbell AD. J. Am. Chem. Soc. 2006, 128: 2514

18 Donohoe TJ. Bataille CJR. Gattrell W. Kloesges J. Rossignol E. Org. Lett. 2007, 9: 1725

19 Torssell S. Somfai P. Org. Biomol. Chem. 2004, 2: 1643

20 Duclos RI. Chem. Phys. Lipids 2001, 111: 111