1: H2 / 10percent Pd/C / ethyl acetate / 24 h / 760 Torr 2: Pb(NO3)2, Et3N / CH2Cl2 / 48 h / Ambient temperature 3: 94 percent / DIBAL / toluene / 0.5 h / -78 °C 4: 1) N-chlorosuccinimide, Me2S, 2) NEt3 / 1) toluene, -25 deg C, 5.5 h, 2) 20 min. 5: 91 percent / tetrahydrofuran / 1 h / -40 deg C to r.t. 6: 1) N-chlorosuccinimide, Me2S, 2) NEt3 / 1) toluene, -25 deg C, 5.5 h 2) 20 min 7: HBr, H2O / diethyl ether / 0.5 h / 0 °C 8: NaHCO3, Na2CO3 / H2O / 2.5 h / Ambient temperature 9: 80 percent / pyridine / 20 h / 0 °C 10: pyridine / CH2Cl2 / 0.33 h / -15 °C 11: 1) Bu4NOAc, 2) DMAP, Py / 1) CH3CN, 40 deg C, 50 min, 2) 3 h, r.t. 12: 93 percent / NaBH4 / ethanol 13: 93 percent / K2CO3 / methanol / 1 h / 0 °C 14: 1) methyl triflate, 2) N-methylimidazole / 1) THF, 0 deg C, 40 min, 2) THF 15: 89 percent / H2, NaOAc / 10percent Pd/C / methanol 16: 95 percent / CF3COOH / H2O; dioxane View Scheme

1: H2 / Pd-C / ethyl acetate / 6 h 2: aq. Na2CO3 / CH2Cl2 / 0.5 h / Ambient temperature 3: 95 percent / Dowex 50W-X8 resin, water / methanol / 16 h / Ambient temperature; further catalysts and solvents 4: 78 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 5: 95 percent / H2, sodium acetate / Pd-C / methanol / 10 h 6: 89 percent / Dowex 50W-X8, water / tetrahydrofuran / Heating View Scheme

1: 96 percent / trifluoroacetic acid, water 2: 91 percent / camphor sulfonic acid 3: 75 percent / pyridine / CH2Cl2 4: 84 percent / acetic acid, water 5: 71 percent / imidazole / dimethylformamide 6: 95 percent / pyridine / CH2Cl2 7: 86 percent / 1.) H2; 2.) sodium acetate / 1.) palladium black / 1.) ethyl acetate; 2.) acetonitrile 8: lithium triethylborohydride / tetrahydrofuran 9: 1percent HCl / methanol View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1: p-TsOH<br />2: pyridine / CH₂Cl₂ <br />3: 97 percent / sodium azide / dimethylformamide / 12 h / 20 &deg;C<br /> <br /> &nbsp;