Multi-step reaction with 10 steps
1: 72 percent / HCl, H2 / 5percent Pd/C / methanol / 5 h / Ambient temperature
2: 98 percent / p-toluenesulfonic acid / 10 h / Heating
3: 1.) O3, 2.) LiOH / 1.) CH2Cl2, -78 deg C, 30 min, 2.) THF, RT, 2 h
4: 73 percent / camphorsulfonic acid / benzene / 2 h / Heating
5: 72 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
6: 93 percent / 4-(dimethylamino)pyridine, pyridine / 5 h / Ambient temperature
7: 95 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating
8: 95 percent / HCl / acetone / 6 h / Ambient temperature
9: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, 0 deg C, 30 min
10: 50 percent / LDA / tetrahydrofuran / 0.17 h / -78 °C
With
pyridine; hydrogenchloride; dmap; lithium hydroxide; lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; hydrogen; toluene-4-sulfonic acid; ozone; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; acetone; benzene;
DOI:10.1021/jo00376a049