Asymmetric synthesis of N, O, O, O-tetra-acetyl d- lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer

The highly diastereoselective conjugate addition of lithium ( S)- N-benzyl- N-(α-methylbenzyl)amide to a γ-silyloxy-α,β-unsaturated ester and 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-p...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 18; no. 21; pp. 2510 - 2513
Main Authors Abraham, Elin, Candela-Lena, José I., Davies, Stephen G., Georgiou, Matthew, Nicholson, Rebecca L., Roberts, Paul M., Russell, Angela J., Sánchez-Fernández, Elena M., Smith, Andrew D., Thomson, James E.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.10.2007
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ALCOHOLS
ROUTE
CYTOTOXIC ANHYDROPHYTOSPHINGOSINE
CHEMICAL-SHIFTS
(2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID
COMPONENT
STEREOSELECTIVE-SYNTHESIS
DERIVATIVES
IODOXYBENZOIC ACID IBX
MARINE SPONGE
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Summary:The highly diastereoselective conjugate addition of lithium ( S)- N-benzyl- N-(α-methylbenzyl)amide to a γ-silyloxy-α,β-unsaturated ester and 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, jaspine B (pachastrissamine) and its C(2)-epimer.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2007.10.026