Multi-step reaction with 7 steps
1: 2,6-lutidine, DMAP / CH2Cl2 / 2 h / 0 °C
2: 1) 9-BBN 2) 1N aq. NaOH, 30percent aq. H2O2 / 1) THF, 4h, 0 deg C 2) 12h, r.t.
3: 86 percent / Dess-Martin periodinane, pyridine / CH2Cl2 / 1.5 h / Ambient temperature
4: 1) nBu2BOTf, iPr2NEt 2) 30percent aq. H2O2, aq. pH 7 phosphate buffer / 1) CH2Cl2, a) 10 min, -78 deg C b) to r.t., 40 min 2) MeOH, 1h
5: 2,6-lutidine, / CH2Cl2 / 2 h / 0 °C
6: 1) nBuLi / 1) THF, hexane, 30 min, 0 deg C 2) THF, 2h, 0 deg C
With
pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; pH 7 phosphate buffer; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
DOI:10.1021/jo00296a042