1: SeO2 / aq. ethanol; pyridine / 1 h / Heating 2: NaBH4 / diethyl ether; methanol / 0.5 h 3: 6.3 percent / BF3-etherate / CH2Cl2 / 1.5 h 4: 79 percent / H2 / PtO2 / ethanol / 10 h / 760 Torr / Ambient temperature 5: 48 percent / RuO2*xH2O/NaIO4 / CCl4 / 2.5 h / 20 °C 6: 5 mg / K2CO3 / m-xylene / 5 h / Heating 7: diisopropylamine/n-BuLi / hexane; tetrahydrofuran / 1.5 h 8: NaIO4 / CH2Cl2; H2O / 0.58 h / Ambient temperature 9: toluene / 5 h / Heating 10: 77 percent / DIBAL / tetrahydrofuran / 20 h View Scheme

in toluene T=-75°C; Paterno-Buechi reaction; 6 h; Inert atmosphereUV-irradiation; regioselective reaction;

in toluene T=-75°C; Paterno-Buechi reaction; 6 h; Inert atmosphereUV-irradiation; regioselective reaction;

in pentane 2 h; Irradiation; Further byproducts given;

potassium tert-butylate; 18-crown-6 ether in tetrahydrofuran 2 h; Heating;

pyridinium chlorochromate in dichloromethane 18 h; Heating;

in cyclohexane Irradiation;

in toluene T=-75°C; Paterno-Buechi reaction; 6 h; Inert atmosphereUV-irradiation; regioselective reaction;

1: 66 percent / tetrahydrofuran / 15 h / -30 °C 2: KOC(CH3)3 / tetrahydrofuran / 3 h / 0 °C View Scheme

potassium tert-butylate in tetrahydrofuran Yield given;