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

Journal article

The highly diastereoselective anti-aminohydroxylation of (E)-gamma-tri-iso-propylsilyloxy-alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-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 Prosopis alkaloid deoxoprosophylline (26% yield over 7 steps).

Authors: Abraham, E; Brock, E; Candela-Lena, J; Davies, S; Georgiou, M

• Publication status: Published
• Journal: Organic and biomolecular chemistry
• Volume: 6
• Issue: 9
• Pages: 1665-1673
• Publication date: 2008-05-01
• DOI: 10.1039/b801671b
• EISSN: 1477-0539
• ISSN: 1477-0520
• Language: English
• Keywords: Amides; Molecular Conformation; Sphingosine; Benzylamines; Lithium; Organometallic Compounds; Stereoisomerism; Piperidines; Oxidation-Reduction