Multi-step reaction with 15 steps
1: 90 percent / triethylamine / 5 h / 4125330 Torr / Ambient temperature
2: AcOH / H2O / Ambient temperature
3: CSA / acetone / Ambient temperature
4: t-BuONa, KMnO4, MgSO4 / H2O; benzene / Ambient temperature
5: K2CO3 / methanol / Ambient temperature
6: 98 percent / n-BuLi / tetrahydrofuran / Ambient temperature
7: 1.) AcOH, 2.) CSA / 1.) H2O, room temperature, 2.) CH2Cl2, room temperature
8: 1.) BH3*Me2S, 2.) 15percent NaOH, 30percent H2O2 / 1.) THF, room temperature, 2.) room temperature
9: 81 percent / pyridine / Ambient temperature
10: LiAlH4 / diethyl ether / 0 °C
11: KH / tetrahydrofuran / 0 °C
12: H2 / Raney Ni / ethanol / Ambient temperature
13: AcOH / H2O / Ambient temperature
14: DDQ / CH2Cl2 / Ambient temperature
15: 51 percent / Ag2CO3-celite / benzene / Heating
With
sodium hydroxide; potassium permanganate; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide borane complex; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; potassium hydride; magnesium sulfate; potassium carbonate; acetic acid; silver carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium t-butanolate;
nickel;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; triethylamine; acetone; benzene;
DOI:10.1016/0040-4039(94)88288-6