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Synthesis of 5E-1-deoxy-sphingosine (6). Reagents and conditions: (a) Boc2O, 1 M NaOH, dioxane, −10 °C to r.t., 4 h; (b) Me(MeO)NH.HCl, EDCI.HCl, NMM, DCM, −15 °C, 2 h; (c) (i) Mg, 1,2-DBE, 1-allylbromide, Et2O, 3 h, (ii) 2, Et2O, 0 °C- r.t., 3 h; (d) TBLAH, EtOH, −78 °C, 2 h; (e) 1-tetradecene, p-benzoquinone (10 mol%), CuI (2 mol%), Grubbs 2nd generation cat. (10 mol%), d-chloroform, r.t., 12 h; (f) AcCl, MeOH, 0 °C-r.t., 2 h.
