silica gel; copper(II) sulfate in dichloromethane 24 h; Heating;

in acetone 5 h; Ambient temperature;

3 A molecular sieve; pyridinium chlorochromate in benzene 5 h; Heating;

1: 85 percent / Zn, Et2AlCl / tetrahydrofuran; hexane / 2 h / 0 °C 2: 85 percent / Na / 24 h / Heating 3: 95 percent / DIBAL-H / toluene / 0.08 h / -20 °C 4: 98 percent / m-chloroperoxybenzoic acid (MCPBA) / methanol / 0.25 h / Ambient temperature 5: 98 percent / aq. HClO4 / methanol 6: pyridine / Ambient temperature View Scheme

(i) LDA, toluene, (ii) FClO3, THF, (iii) aq. HCl, EtOH; Multistep reaction;