Multi-step reaction with 11 steps
1: NaBH4 / aq. ethanol; CHCl3 / 7 h / 0 °C
2: pyridine / 1) 0 grad C, 10 min; 2) 10-15 grad C, 30 hr
3: sym-collidine / 3 h / Heating
4: 1) O2 / 1) methylene blue, sunlight / 1)pyridine, 35 hr; 2) Ac2O, 30 grad C, 45 min, 60 grad C, 1 hr
5: 86.7 percent / LAH / diethyl ether / 6 h / 0 °C
6: 80 percent / p-toluenesulphonic acid / 0.33 h / 12 °C
7: 80 percent / pyridinium chromate-on-silica gel / CH2Cl2; acetic acid / 6 h / Ambient temperature
8: 88.4 percent / p-toluenesulphonic acid / acetic acid; acetic anhydride / 48 h / Ambient temperature
9: 67 percent / NaBH3CN, 4A molecular sieves / methanol / 80 h / Ambient temperature
10: 1) KOH; 2) MnO2 / 1) MeOH, reflux, 4 hr; 2) C6H6, rt, 12 hr
11: KOH / aq. ethanol / 2 h / Ambient temperature
With
2,4,6-trimethyl-pyridine; manganese(IV) oxide; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; pyridinium chromate-on-silica gel; 4 A molecular sieve; oxygen; sodium cyanoborohydride;
methylene blue; toluene-4-sulfonic acid;
In
pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; acetic anhydride; acetic acid;
DOI:10.1016/S0040-4020(01)92368-3