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

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

Research output: Contribution to journalReview articlepeer-review

103 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)1665-1673
Number of pages9
JournalOrganic & Biomolecular Chemistry
Volume6
Issue number9
DOIs
Publication statusPublished - 2008

Keywords

  • D-RIBO-PHYTOSPHINGOSINE
  • STEREOSELECTIVE TOTAL-SYNTHESIS
  • D-ERYTHRO-SPHINGOSINE
  • ENANTIOSELECTIVE TOTAL-SYNTHESIS
  • INTRAMOLECULAR N-ALKYLATION
  • PIPERIDINE RING FORMATION
  • CHIRAL BUILDING-BLOCK
  • CYTOTOXIC ANHYDROPHYTOSPHINGOSINE
  • EFFICIENT SYNTHESIS
  • FORMAL SYNTHESIS

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