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 language | English |
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Pages (from-to) | 1665-1673 |
Number of pages | 9 |
Journal | Organic & Biomolecular Chemistry |
Volume | 6 |
Issue number | 9 |
DOIs | |
Publication status | Published - 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