symmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer
Abraham E., Candela-Lena JI., Davies SG., Georgiou M., Nicholson RL., Roberts PM., Russell AJ., Sánchez-Fernández EM., Smith AD., Thomson JE.
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. © 2007 Elsevier Ltd. All rights reserved.