Multi-step reaction with 13 steps
1: 1.) NaH / 1.) DMF, RT, 40 min, 2.) DMF, RT, 13 h
2: 0.8 N H2SO4 / methanol / 48 h / Ambient temperature
3: NaIO4 / methanol / 2.5 h / Ambient temperature
4: NaBH4 / methanol / 2 h / Ambient temperature
5: pyridine / 2 h / Ambient temperature
6: 1.) TMSOTf, 2.) Et3SiH / 1.) CH2Cl2, RT, 0.5 h, 2.) CH2Cl2, RT, 18 h
7: H2 / 10percent Pd/C / methanol / 20 h / Ambient temperature
8: DMAP / pyridine / 23 h / Ambient temperature
9: 623 mg / Et3N, DMAP / CH2Cl2 / 2 h / Ambient temperature
10: 32 percent / K2CO3, 18-crown-6-ether / dimethylformamide / 20 h / 120 °C
11: methanolic ammonia / 48 h / Ambient temperature
12: methanol / 11 h / Ambient temperature
13: DMAP / pyridine / 2 h / Ambient temperature
With
pyridine; triethylsilane; dmap; sodium tetrahydroborate; sodium periodate; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; ammonia; hydrogen; sodium hydride; potassium carbonate; triethylamine;
palladium on activated charcoal;
In
pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(96)00007-5