Multi-step reaction with 9 steps
1: Ph3P, DEAD / diethyl ether / Ambient temperature
2: NaOMe / methanol / Ambient temperature
3: 79 percent / 5percent aq. NaOH / tetrabutylammonium hydrogen sulfate / CH2Cl2 / 1 h / -5 °C
4: 1.) OsO4, N-methylmorpholine N-oxide, 2.) NaIO4 / 1.) t-butyl alcohol, THF, H2O, r.t., overnight, 2.) THF, H2O, r.t., 30 min
5: HCl / 1 h
6: Na, liquid NH3 / diethyl ether / 0.5 h
7: pyridine / Ambient temperature
8: 72 percent / stannic chloride / CH2Cl2 / 24 h / Ambient temperature
9: 8 percent / I2, chlorodiphenylphosphine, imidazole / acetonitrile
With
pyridine; 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium periodate; osmium(VIII) oxide; ammonia; iodine; sodium methylate; sodium; tin(IV) chloride; 4-methylmorpholine N-oxide; chloro-diphenylphosphine; triphenylphosphine; diethylazodicarboxylate;
tetra(n-butyl)ammonium hydrogensulfate;
In
methanol; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jo00086a032