Multi-step reaction with 12 steps
1: 80 percent / diphenylphosphorazide; DBU / toluene / 10 h
2: hydrogen / 10 percent Pd/C / ethyl acetate / 0.67 h / 750.06 Torr
3: 2.57 g / triethylamine / CH2Cl2 / 3 h / 0 - 20 °C
4: 92 percent / m-chloroperbenzoic acide / CH2Cl2 / 4 h / 20 °C
5: 94 percent / BF3*Et2O; molecular sieves 4 Angstroem / tetrahydrofuran / 3 h / 0 °C
6: 89 percent / CeCl3*7H2O; NaBH4 / methanol / 0.67 h / -30 °C
7: 87 percent / triethylamine / CH2Cl2 / 1 h / 20 °C
8: 92 percent / 4 Angstroem molecular sieves; m-chloroperbenzoic acid; BF3*Et2O / CH2Cl2 / 2 h / 20 °C
9: 89 percent / hydrogen / 10 percent Pd/C / methanol / 2 h / 750.06 Torr
10: 93 percent / TBAF / tetrahydrofuran / 2 h
11: 80 percent / NaIO4; RuCl3 / H2O; CCl4; acetonitrile / 2 h
12: 62 percent / naphthalene; sodium / tetrahydrofuran / 0.5 h / -78 °C
With
ruthenium trichloride; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; naphthalene; 4 A molecular sieve; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; ethyl acetate; toluene; acetonitrile;
DOI:10.1016/S0040-4020(02)00674-9