Multi-step reaction with 13 steps
1: dimethylsulfide borane complex / tetrahydrofuran / 17 h / 0 - 20 °C
2: triethylamine / dichloromethane / 1.5 h / 0 - 20 °C
3: triethylamine / dichloromethane / 4 h / 0 - 20 °C
4: triphenylphosphine; triethylamine; formic acid; palladium diacetate / N,N-dimethyl-formamide / 2 h / 60 °C
5: lithium borohydride / tetrahydrofuran / 20 h / 0 - 50 °C / Inert atmosphere
6: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 0 - 20 °C
7: tetrahydrofuran / 1 h / 0 - 20 °C
8: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 0.5 h / 0 - 20 °C
9: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 20 °C
10: 3-chloro-benzenecarboperoxoic acid; scandium tris(trifluoromethanesulfonate) / dichloromethane / 72 h / 0 - 20 °C / Inert atmosphere
11: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2.5 h / 0 - 20 °C
12: hydrogenchloride / tetrahydrofuran; water / 24 h / 0 - 20 °C
13: Amberlyst-15 / acetonitrile / 1 h / 0 - 20 °C
With
hydrogenchloride; lithium borohydride; formic acid; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; palladium diacetate; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; scandium tris(trifluoromethanesulfonate);
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
10: |Baeyer-Villiger Ketone Oxidation;
DOI:10.1055/s-0033-1339484