Multi-step reaction with 18 steps
1.1: diisopropylamine; BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
1.2: 78 percent / tetrahydrofuran; hexane / 2 h / 20 °C
2.1: diphenylphosphoryl azide; triethylamine / benzene / 0.5 h / Heating
2.2: 65 percent / benzene / 5 h / Heating
3.1: 94 percent / osmium tetroxide; N-methylmorpholine N-oxide / acetone; H2O; 2-methyl-propan-2-ol / 5 h / 20 °C
4.1: 86 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 4 h / 20 °C
5.1: 92 percent / imidazole / dimethylformamide / 4.5 h / 20 °C
6.1: H2 / 5 percent Pd/C / methanol / 3 h
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 3.5 h / Heating
8.1: potassium carbonate / acetonitrile / 2.5 h / 20 °C
9.1: 964 mg / tetrabutylammonium fluoride / tetrahydrofuran / 15 h / 20 °C
10.1: 82 percent / diphenylphosphoryl azide; triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C
11.1: 75 percent / H2 / 5 percent Pd/C / methanol / 1.5 h
12.1: lithium hydroxide / H2O / 0.67 h / 20 °C
13.1: 234 mg / diphenylphosphoryl azide; triethylamine / dimethylformamide / 1.5 h / 20 °C
14.1: 56 percent / sodium hydride / tetrahydrofuran / 1.5 h / 20 °C
15.1: lithium diisopropylamide / tetrahydrofuran / 0.33 h / -78 °C
15.2: 85 percent / tetrahydrofuran / 0.33 h / -78 °C
16.1: triethylamine / CH2Cl2 / 1 h / 0 °C
17.1: 14.1 mg / potassium tert-butoxide / tetrahydrofuran / 1 h / 0 °C
18.1: lithium aluminium hydride; aluminium chloride / diethyl ether / 1 h / 20 °C
With
1H-imidazole; dmap; lithium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; diphenylphosphoranyl azide; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4020(02)00436-2