Multi-step reaction with 9 steps
1: KO-t-Bu / 2-methyl-propan-2-ol / 3 h / Heating
2: 6 h / Heating
3: methanol. NaOMe / 1 h / Ambient temperature
4: pyridine / CH2Cl2 / 1 h / 0 °C
5: 1.) LiCl, PdCl
26H5)3>2 / 1.) DMF, RT, 15 min, 2.) DMF, RT, 12 h
6: 1.) 9-BBN, 2.) aq. H2O2 / 1.) THF, RT, 48 h, 2.) THF, from 0 deg C to RT, 2 h
7: 4.4 g / LAH / tetrahydrofuran / 1 h / 5 - 10 °C
8: MnO2 / CH2Cl2 / 18 h / Ambient temperature
9: 1.) NaH / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 5 h
With
pyridine; manganese(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; potassium tert-butylate; dihydrogen peroxide; sodium methylate; sodium hydride; lithium chloride;
In
tetrahydrofuran; dichloromethane; tert-butyl alcohol;
DOI:10.1021/jm950699x