1: 62 percent / KOH, hydrazine / bis-(2-hydroxy-ethyl) ether / 1.) 100 deg C, 1.5 h, 2.) 210 deg C, 4 h 2: 1.) O3, 2.) Me2S / 1.) EtOAc, -40 deg C, 6.5 h, 2.) EtOAc, from -40 deg C to RT 3: 91 percent / pyridinium tosylate / benzene / 0.25 h / Heating 4: 1.) KMnO4, 2.) Pb(OAc)4 / 1.) a) tert-BuOH, H2O, RT, 40 min, b) tert-BuOH, H2O, 40 deg C, 10 min, 2.) MeOH, RT, 1h 5: 82 percent / m-CPBA / CH2Cl2 / 12 h / Heating 6: 100 percent / KOH, EtOH / 0.5 h 7: FeCl3 / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 24 h 8: 384 mg / sodium acetate / methanol / 3 h / Heating 9: 70 percent / CuI / tetrahydrofuran; various solvent(s) / 1 h 10: 1.) LDA / 1.) dimethoxyethane, -40 deg C, 2.) dimethoxyethane, 50 deg C, 30 min 11: 1.) LDA, 2.) phenylselenyl chloride, 3.) pyridine, 30percent H2O2 12: 90 percent / NH3, Li / tetrahydrofuran / 1 h / -33 °C 13: 95 percent / L-Selectride / tetrahydrofuran / 2.5 h / -78 - 0 °C 14: 1.) BH3, 2.) 30percent aq. H2O2, aq. NaOH / 1.) THF, 0 deg C to RT, 1.5 h, 2.) THF, water, overnight 15: 48 percent / p-toluenesulfonic acid / toluene / 2 h / 80 °C View Scheme