Issue 9, 2008

Asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophyllinevialithium amide conjugate addition

Abstract

The highly diastereoselective anti-aminohydroxylation of (E)-γ-tri-iso-propylsilyloxy-α,β-unsaturated esters, viaconjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine (20% yield over 7 steps), the anhydrophytosphingosine jaspine B (10% yield over 9 steps), 2-epi-jaspine B (14% yield over 9 steps), and the Prosopisalkaloid deoxoprosophylline (26% yield over 7 steps).

Graphical abstract: Asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophyllinevialithium amide conjugate addition

Supplementary files

Additions and corrections

Article information

Article type
Paper
Submitted
30 Jan 2008
Accepted
20 Feb 2008
First published
19 Mar 2008

Org. Biomol. Chem., 2008,6, 1665-1673

Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophyllinevialithium amide conjugate addition

E. Abraham, E. A. Brock, J. I. Candela-Lena, S. G. Davies, M. Georgiou, R. L. Nicholson, J. H. Perkins, P. M. Roberts, A. J. Russell, E. M. Sánchez-Fernández, P. M. Scott, A. D. Smith and J. E. Thomson, Org. Biomol. Chem., 2008, 6, 1665 DOI: 10.1039/B801671B

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