Multi-step reaction with 18 steps
1: 83 percent / POCl3 / 1 h / 60 °C
2: 47 percent / i-Pr2NLi / tetrahydrofuran / 2 h / -75 °C
3: 86 percent / 2,6-lutidine / CH2Cl2 / 1 h / Ambient temperature
4: 67 percent / LiAlH4 / diethyl ether / 0.5 h / -10 °C
5: 1) 2percent aq. OsO4, N-methylmorpholine N-oxide, 2) NaIO4 / 1) acetone, t-BuOH, r.t., 16 h, 2) EtOAc, H2O, r.t., 2 h
6: 93 percent / Ag2CO3, celite / benzene / 0.5 h / Heating
7: 1) Et3N, MeSO2Cl, 2) Et3N / 1) benzene, r.t., 2 h, 2) benzene, r.t., 16 h
8: 98 percent / N-methylmorpholine N-oxide, 2percent aq. OsO4 / acetone; 2-methyl-propan-2-ol / 24 h / Ambient temperature
9: 94 percent / Bu4NF / tetrahydrofuran / 1 h / 0 °C
10: 57 percent / 10-camphorsulfonic acid / CH2Cl2 / 16 h / Ambient temperature
11: 82 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature
12: 99 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature
13: 69 percent / DIBAL-H / toluene / 0.5 h / -75 °C
14: 74 percent / 2-fluoro-1-methylpyridinium tosylate, Et3N / CH2Cl2 / 2 h / Ambient temperature
15: 66 percent / trimethylsilyl trifluoromethanesulfonate / diethyl ether / 7 h / 0 °C
16: 40 percent / Bu4NF / tetrahydrofuran; acetonitrile / 3 h / Ambient temperature
17: 58 percent / 7 h
18: 91 percent / Bu4NF / 3 h
With
2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; silver carbonate; lithium diisopropyl amide; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene;