Multi-step reaction with 8 steps
1: 98 percent / BH3*Me2S / tetrahydrofuran / 0 °C
2: 95 percent / Et3N, bis(trimethylsilyl)amine / tetrahydrofuran / Ambient temperature
4: 1.) BH3*Me2S, 2.) 3 N NaOH, 30percent H2O2 / 1.) THF, RT, 3 days 2.) 1 h
5: 84 percent / CBr4, PPh3 / acetonitrile / 1 h / 0 °C
6: 95 percent / lutidine / CH2Cl2 / 0 - 20 °C
7: acetonitrile / 72 h / Heating
8: 1.) NaN(TMS)2 / 1a.) THF, 0 deg C, 1b.) reflux, 90 min, 2a.) -78 deg C, 30 min, 2b.) RT, 14 h
With
sodium hydroxide; carbon tetrabromide; dimethylsulfide borane complex; lutidine; dihydrogen peroxide; sodium hexamethyldisilazane; triethylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane;
In
tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo00247a014