Multi-step reaction with 9 steps
1: imidazole, DMAP / dimethylformamide / Ambient temperature
2: sodium iodide / butan-2-one / 5 h / Heating
3: 75 percent / 16.5 h / 155 °C
4: bis(trimethylsilyl)trifluoroacetamide (BSTFA), trimethylsilyl bromide (TMSBr) / CH2Cl2 / 20 h / Ambient temperature
5: dicyclohexylcarbodiimide (DCC), pyridine / 20 h / Ambient temperature
6: 1.) TMSDEA, 2.) oxalyl chloride, DMF / 1.) CH2Cl2, RT, 1 h, 2.) CH2Cl2, 0 deg C - 20 deg C, 1 h
7: 1.) tert-butyllithium / 1.) THF, pentane, -100 deg C, 25 min, 2.) THF, pentane, from -100 deg C to -78 deg C, 30 min
8: tetra-n-butylammonium fluoride, HOAc / tetrahydrofuran / 19 h / Ambient temperature
9: H2 / 10percent Pd/C / methanol / 72 h / 2585.7 Torr
With
pyridine; 1H-imidazole; dmap; bis(trimethylsilyl)trifluoroacetamide; oxalyl dichloride; trimethylsilyl bromide; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; acetic acid; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; N,N-diethyl-1,1,1-trimethylsilanamine; sodium iodide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; butanone;
DOI:10.1021/jm00113a019