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Synthesis of 6E-3-keto-1-deoxy-sphingosine (9). Reagents and conditions: (a) (i) Mg, 1,2-DBE, 4-bromo-1-butene, Et2O, 1 h, (ii) 2, Et2O, 0 °C- r.t., 2 h; (b) 1-tridecene, p-benzoquinone (10 mol%), CuI (2 mol%), Grubbs 2nd generation cat. (10 mol%), d-chloroform, 40 °C, 3 h; (c) AcCl, MeOH, 0 °C-r.t., 2 h.
