1: 97 percent / pyridine / CH2Cl2 / 0 °C 2: 74 percent / 9-BBN; Cs2CO3; H2O / (dppf)PdCl2 / tetrahydrofuran; dimethylformamide / 0 °C View Scheme

2: 56 percent / 4-dimethylaminopyridine / CH2Cl2 / 21 h / 0 - 4 °C 3: 85 percent / tributyltin hydride, di-tert-butyl peroxide / 7.5 h / 50 °C 4: 86 percent / diisobutylaluminum hydride, 2,6-di-tert-butyl-4-methylphenol / toluene / -78 deg C to -20 deg C for 2h and then -20 deg C 1.7h 5: 96 percent / H2 / Lindlar / benzene; cyclohexane; cyclohexene / 13 h / 26 °C / 760 Torr 6: 100 percent 7: 95 percent / (n-C4H9)4NF / tetrahydrofuran / 3 h / 26 °C 8: 20percent NaOH-H2O / 18.3 h / 16 °C 9: Jones reagent / 0.33 h / -30 °C 10: CH3COOH / H2O; tetrahydrofuran / 16 deg C for 1h and 27 deg C for 29h View Scheme

1: 1.) t-butyllithium, 2.) copper(I)iodide, tributylphosphine / 1.) ether, -78 deg C, 2 h, 2.) -78 deg C, 15 min then -40 deg C, 1 h, 3.) -78 deg C, 15 min then -40 deg C, 1 h 2: 30 percent / tributyltin hydride, azobisisobutyronitrile / toluene / Heating 3: 86 percent / hydrogenfluoride, pyridine / acetonitrile / 2.5 h / Ambient temperature 4: 86 percent / pig liver esterase / H2O / 4 h / Ambient temperature View Scheme

1: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C 2: 48 percent / Et3N, pancreatin / various solvent(s) / 7 h / Ambient temperature 3: 67 percent / Et3N, TBAF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: H2O2, NaOH 2: 1.) HCl; 2.) pyridine View Scheme

1: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C 2: 77 percent / Et3N, TBAF / tetrahydrofuran / 3 h / Ambient temperature View Scheme

1: 51 percent / Mo[N(t-Bu)(3,5-diMePh)]3/CH2Cl2 / toluene; CH2Cl2 / 9 h / 80 °C 2: 87 percent / H2; quinoline / Lindlar catalyst / hexane / 760.05 Torr 3: 88 percent / aq. HF / tetrahydrofuran / 1 h View Scheme

1: 1.) t-C4H9Li; copper(I) iodide, tributylphosphine; 3.) triphenyltin chloride / 1.) ether-pentane, -95 deg C, -78 deg C 3h; THF -78 deg C 15 min; 2.) ether, pentane, THF, -78 deg C 3.5 h, HPMA, -78 deg C 30 min; 3.) ether, pentane, THF, HMPA, -30 deg C, 39 h 2: 87 percent / hydrogen, synthetic quinoline / palladium on barium sulfate / benzene; cyclohexane / 1.) 25 deg C, 3 h; 2.) 40 deg C, 4.5 h 3: 1.) L-Selectride; 2.) 3percent H2O2 / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C 4: 85 percent / acetic acid / tetrahydrofuran; H2O / 1.5 h / 55 °C View Scheme

hydrogen; nickel boride in methanol

1: 1.) CuI / 1.) ether, cyclohexane, -70 deg C, 2.) ether, cyclohexane, 0 deg C, 2 h 2: 1.) L-Selectride, 2.) n-Bu4NF / 1.) THF, -78 deg C. 30 min, 2.) THF, RT, 3 h 3: 26 percent / Ph3P, CBr4 / CH2Cl2 / 15 h / Ambient temperature 4: 8 percent / H2O2, CF3COOAg / diethyl ether / 0.5 h / 0 °C 5: 69 percent / NaBH4 / methanol / 0.08 h / 0 °C View Scheme