Multi-step reaction with 9 steps
1: 1.) NaHMDS, 2.) HMPA / 1.) THF, from 0 deg C to 5 deg C, 30 min, 2.) THF, RT, 17 h
2: 1.) O3, pyridine, 2.) Me2S / 1.) CH2Cl2, MeOH, -78 deg C, 2.) CH2Cl2, MeOH, RT, overnight
3: 2-methyl-2-butene, NaClO2 / 2-methyl-propan-2-ol / 0.5 h / Ambient temperature
4: ethyl acetate; diethyl ether / 0.5 h / 0 - 5 °C
5: 70 percent / NaBH4 / methanol / 6 h / Ambient temperature
6: 59 percent / tetrahydrofuran / 7 h / Heating
7: 95 percent / n-Bu3SnH, AIBN / toluene / 4 h / Heating
8: 48percent aq. HF / acetonitrile / 3 h / Ambient temperature
9: aq. LiOH / tetrahydrofuran / 3 h / Ambient temperature
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; 2-methyl-but-2-ene; dimethylsulfide; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; ozone;
In
tetrahydrofuran; methanol; diethyl ether; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0039-128X(97)00088-3