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

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

来源：Organic and Biomolecular Chemistry, 2008, 6(9): 1665-1673.

DOI：10.1039/b801671b

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).

• 出版日期2008