Multi-step reaction with 14 steps
1: 79 percent / PTSA*H2O / CHCl3 / 6 h / Ambient temperature
2: CuI / tetrahydrofuran / -78 °C
3: Et3N / tetrahydrofuran / -78 - 20 °C
4: 3.54 g / NaI, m-CPBA / tetrahydrofuran / 0.33 h / Ambient temperature
5: Bu3SnH, AIBN / benzene / 1 h / Heating
6: 84 percent / TFA / benzene / 0.33 h
7: BF3*Et2O / CH2Cl2 / 3.5 h
8: 57 mg / DBU / CH2Cl2 / 1 h / Ambient temperature
9: 1.) BH3*Me2S, 2.) H2O2, NaOH / 1.) THF, rt, 4.5 h, 2.) THF, H2O, rt, 12 h
10: CH2Cl2; triethylamine / 1.5 h / Ambient temperature
11: 80 percent / NaN3, 18-crown-6 / dimethylformamide / 1.5 h / 100 °C
12: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature
13: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h
14: 42 percent / H2O; formic acid / 12 h / 120 °C
With
chromium(VI) oxide; sodium hydroxide; copper(l) iodide; sodium azide; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; sulfuric acid; boron trifluoride diethyl etherate; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic acid; sodium iodide;
In
tetrahydrofuran; formic acid; dichloromethane; chloroform; water; triethylamine; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/ja9643432