Multi-step reaction with 14 steps
1: 1.) diisopropylamine, BuLi / 1.) THF, hexane, a) -50 deg C, 15 min, b) RT, 1 h, 2.) -78 deg C, 3 h
2: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr / Ambient temperature
3: p-TsOH, / CHCl3 / Ambient temperature
4: Jones' reagent / acetone / 1 h / 10 °C
5: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature
6: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C
7: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h
8: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C
9: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature
10: benzenesulfonylchloride, pyridine / 0 °C
11: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C
12: 38 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 2 h / Ambient temperature
13: 63 percent / 0.02 N NaOH / dioxane; H2O / Ambient temperature
14: 33 percent / pivaloyl chloride, Et3N / dimethylformamide / 2 h / -5 °C
With
pyridine; potassium hydroxide; sodium hydroxide; n-butyllithium; jones' reagent; trifluorormethanesulfonic acid; hydrogen; pyridinium p-toluenesulfonate; pivaloyl chloride; toluene-4-sulfonic acid; triethylamine; diisopropylamine; benzenesulfonyl chloride; triphenylphosphine; diethylazodicarboxylate;
platinum(IV) oxide; palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00241a018