1: 84 percent / methanol / 3 h / Heating 2: 1.) Hg(OAc)2; 2.) NaBH4 / 1.) THF, 4 deg C, 1.5 h 3: 45 percent / Jones reagent 4: 75 percent / potassium hydride, triethylborane / tetrahydrofuran / 3 h / 0 - 25 °C 5: 74 percent / potassium tert-butoxide / 1,2-dimethoxy-ethane / 6 h / 45 °C 6: 75 percent / DIBAL / benzene / 5 h / 25 °C 7: 75 percent / TFA, ozone / CH2Cl2 / -78 °C View Scheme

1: 82 percent / methanol / 100 h / 72 °C 2: 70 percent / Hg(OAc)2, NaOH, NaBH4 / tetrahydrofuran / 1.5 h / 4 °C View Scheme

iodine in acetonitrile 2 h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: 70 percent / LiAlH4 / diethyl ether / 24 h / Heating 2: 62 percent / Jones-reagent / acetone / Ambient temperature 3: 88 percent / 85percent m-chloroperbenzoic acid / CH2Cl2 / 5 h / Ambient temperature View Scheme

hydrogen; platinum(IV) oxide in ethanol 24 h; Ambient temperature;

hydrogen; palladium on activated charcoal in various solvent(s) T=39.9°C; var. time reaction, other catalyst; E(a); Product distributionThermodynamic data;

hydrogen; palladium on activated charcoal in various solvent(s) T=39.9°C; var. time reaction, other catalyst; E(a); Product distributionThermodynamic data;

N,N,N',N',N'',N''-hexamethylphosphoric triamide; lithium diethylamide in diethyl ether

1: aq. H2SO4 2: pyridine 4: K2CO3, methanol 5: 90 percent / H2 / 5percent Pd/C / methanol View Scheme

trifluorormethanesulfonic acid; N-ethyl-N,N-diisopropylamine 1.) DMSO, 23 deg C; 2.) CH2Cl2, -78 deg C, then room temp.; Yield given. Multistep reaction;