Multi-step reaction with 5 steps
1: 88 percent / LDA, LiCl / tetrahydrofuran / 0.33 h / 0 °C
2: 1.) LiAl(OEt)3H, 2.) HCl / 1.) hexane/THF, -78 deg C to 0 deg C, 1 h, 2.) TFA, 20 deg C, 5 min
3: 1.) B-methoxybis(2-isocaranyl)borane, 2.) H2O2 / 1.) Et2O, -78 deg C, 4 h, 2.) aq. NaOH, reflux, 16 h
4: 2.) Oxone / 1.) AIBN / 1.) PhMe, 90 deg C, 72 h, 2.) MeOH/H2O, 20 deg C, 4 h
5: 96 percent / 2,6-lutidine / CH2Cl2 / 0.33 h / -78 °C
With
2,6-dimethylpyridine; hydrogenchloride; Oxone; B-methoxy-bis(2-isocaranyl)borane; dihydrogen peroxide; lithium triethoxyaluminum hydride; lithium chloride; lithium diisopropyl amide;
2,2'-azobis(isobutyronitrile);
In
tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(97)00885-X