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

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...

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Published in:Organic & biomolecular chemistry 2008-01, Vol.6 (9), p.1665-1673
Main Authors: Abraham, Elin, Brock, E Anne, Candela-Lena, José I, Davies, Stephen G, Georgiou, Matthew, Nicholson, Rebecca L, Perkins, James H, Roberts, Paul M, Russell, Angela J, Sánchez-Fernández, Elena M, Scott, Philip M, Smith, Andrew D, Thomson, James E
Format: Article
Language:English
Subjects:
Amides - chemistry
Benzylamines - chemistry
Lithium - chemistry
Molecular Conformation
Organometallic Compounds - chemistry
Oxidation-Reduction
Piperidines - chemical synthesis
Piperidines - chemistry
Sphingosine - analogs & derivatives
Sphingosine - chemical synthesis
Sphingosine - chemistry
Stereoisomerism
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Summary: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).
ISSN:1477-0520
1477-0539
DOI:10.1039/b801671b