Multi-step reaction with 9 steps
1: 1.) n-BuLi, 2.) B(OMe)3, 3.) 30percent aq. H2O2, aq. NaOH
2: 79 percent / Et3N / CH2Cl2 / 21 h / Ambient temperature
3: 100 percent / oxalyl chloride, DMF / CH2Cl2 / 19 h / Ambient temperature
4: 1.) s-BuLi / 1.) THF, cyclohexane, -78 deg C, 20 min, 2.) THF, cyclohexane, -78 deg C, 50 min
5: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h
6: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, 3.5 h
7: Pd((S)-BINAP)2, pentamethylpiperidine / toluene / 22 h / 110 °C
8: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 6.5 h
9: aq. ceric ammonium nitrate / acetonitrile / 0.17 h / 0 °C
With
sodium hydroxide; n-butyllithium; oxalyl dichloride; ammonium cerium(IV) nitrate; Pd(BINAP)2; Trimethyl borate; pentamethylpiperidine; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sec.-butyllithium; sodium hydride; triethylamine; N,N-dimethyl-formamide;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; ethyl acetate; toluene; acetonitrile;
DOI:10.1021/ja960807k
