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

Elin Abraham, Jose I. Candela-Lena, Stephen G. Davies, Matthew Georgiou, Rebecca L. Nicholson, Paul M. Roberts, Angela J. Russell, Elena M. Sanchez-Fernandez, Andrew D. Smith, James E. Thomson

Research output: Contribution to journalArticlepeer-review

80 Citations (Scopus)

Abstract

The highly diastereoselective conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a gamma-silyloxy-alpha,beta-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. (c) 2007 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)2510-2513
Number of pages4
JournalTetrahedron: Asymmetry
Volume18
Issue number21
DOIs
Publication statusPublished - 22 Oct 2007

Keywords

  • IODOXYBENZOIC ACID IBX
  • CYTOTOXIC ANHYDROPHYTOSPHINGOSINE
  • STEREOSELECTIVE-SYNTHESIS
  • (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID
  • CHEMICAL-SHIFTS
  • MARINE SPONGE
  • D-XYLOSE
  • DERIVATIVES
  • ALCOHOLS
  • CONFIGURATION

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