Multi-step reaction with 6 steps
1: 92 percent / LiBH4 / tetrahydrofuran / 15 h / 5 °C
2: 98 percent / TEA, 4-DMAP / dimethylformamide / 3 h / Ambient temperature
3: 90 percent / RuO2 hydrate, 10percent aqueous NaIO4 / ethyl acetate / 1 h / Ambient temperature
4: 1.) n-butyllithium, diisopropylamine / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 1h; 3.) room temperature, 1h
5: 78 percent / p-toluenesulphonic acid / methanol / 2 h / Ambient temperature
6: 1.) pyridinium dichromate; 2.) DCC, 4-DMAP / 1.) DMF, 15 h, 40 deg C; 2.) CH2Cl2, 3 h, room temperature
With
dmap; ruthenium(IV) oxide; sodium periodate; dipyridinium dichromate; lithium borohydride; n-butyllithium; TEA; toluene-4-sulfonic acid; diisopropylamine; dicyclohexyl-carbodiimide;
In
tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;