Multi-step reaction with 11 steps
1: 90 percent / m-chloroperbenzoic acid / CHCl3 / 3 h / 5 °C
2: 93 percent / p-toluenesulfonic acid / toluene / 1 h / Heating
3: toluene / 6 h / Heating
4: triethylamine / toluene; benzene / 2 h / Heating
5: 53 percent / sodium borohydride / benzene; methanol / 2 h / 5 °C / Irradiation
6: 1.) ozone, 2.) lithium aluminum hydride / 1.) methylene dichloride, -30 deg C, 10 min, 2.) THF, ether, reflux, 2 h
7: 89 percent / pyridine / 3.5 h / 0 °C
8: 74 percent / sodium borohydride / dimethylsulfoxide / 8 h / 80 °C
9: 24 percent / thionyl chloride / benzene / 1.5 h / Heating
10: 94 percent / sodium, liquid ammonia / tetrahydrofuran / 1 h
11: 89 percent / phenylseleninic anhydride, indole / tetrahydrofuran / 1.5 h / 40 °C
With
pyridine; indole; sodium tetrahydroborate; lithium aluminium tetrahydride; thionyl chloride; benzeneseleninic anhydride; ammonia; sodium; toluene-4-sulfonic acid; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; chloroform; dimethyl sulfoxide; toluene; benzene;
DOI:10.1248/cpb.39.23