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Issue 9, 2008
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Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophyllinevialithium amide conjugate addition

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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

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The article was received on 30 Jan 2008, accepted on 20 Feb 2008 and first published on 19 Mar 2008


Article type: Paper
DOI: 10.1039/B801671B
Citation: Org. Biomol. Chem., 2008,6, 1665-1673
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    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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