Multi-step reaction with 12 steps
3: 1.) LiN(TMS)2 / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 10 min
4: BH3*Me2S / tetrahydrofuran / 1 h
5: imidazole / dimethylformamide
6: NaOMe / methanol / 0.25 h / 0 °C
7: 1.) LiN(TMS)2, 2.) ethyl(dimethylaminoethyl) carbodiimide HCl, DMAP / 1.) THF, 0 deg C, then 25 deg C, 2.) Et2O
8: 1.) NaIO4, 2.) pyr. / 1.) H2O, 2.) toluene, reflux, 3 h
9: H2 / Pd/C / ethyl acetate
10: LAH / tetrahydrofuran / 2 h / -10 °C
11: PPTS / CH2Cl2
With
pyridine; 1H-imidazole; dmap; sodium periodate; lithium aluminium tetrahydride; dimethylsulfide borane complex; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)80903-5