Multi-step reaction with 9 steps
1: 78 percent / toluene / 9 h / Heating
2: 90 percent / DIBAL-H / CH2Cl2; toluene / 1 h / -78 °C
3: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, 20 min, -60 deg C, 2) 2h 15 min, -60 deg C
5: 1) Me3Al / 1) CH2Cl2, toluene, 30 min, r.t., 2) CH2Cl2, 18 h, -20 deg C
6: 91 percent / imidazole / dimethylformamide / 18 h / Ambient temperature
7: 1) OsO4, N-methylmorpholine oxide, 2) NaIO4, NaHCO3 / 1) t-BuOH, water, THF, 3 h, r.t., 2) water, 45 min
8: 1) TiCl4, Et3N / 1) CH2Cl2, 1 h, 0 deg C, 2) CH2Cl2, 0 deg C, 3.3 h
9: 88 percent / K2CO3 / tetrahydrofuran / 2 h / Heating
With
1H-imidazole; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; trimethylaluminum; titanium tetrachloride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00054a035