Multi-step reaction with 10 steps
1: 99 percent / VO(acac)2, t-BuOOH / CH2Cl2; decane / 0 - 20 °C
2: periodic acid / tetrahydrofuran; H2O / 0 - 20 °C
3: benzene; methanol; hexane / 0.5 h / Ambient temperature
4: NaBH4 / methanol / 0 - 20 °C
5: 13.2 g / imidazole / dimethylformamide / 0.5 h
6: 98 percent / i-Bu2AlH / tetrahydrofuran; hexane / 0.75 h / -78 °C
7: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH2Cl2, 25 min, 2.) CH2Cl2
8: 1.) KO-t-Bu / 1.) THF, 15 min, 2.) THF
9: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C -> room temperature
10: 1.) BuLi / 1.) THF, hexane, 1 h, 2.) THF, hexane, room temperature, overnight
With
1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; bis(acetylacetonate)oxovanadium; potassium tert-butylate; diisobutylaluminium hydride; dimethyl sulfoxide; periodic acid; triethylamine;
In
tetrahydrofuran; methanol; decane; hexane; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo970360d