Multi-step reaction with 12 steps
1: 1.) aq. NaOH / 1.) ethanol, RT, 0.5 h, 2.) pentane, reflux, 48 h
2: CH2Cl2 / 336 h / 5 °C
3: 1.) potassium hexamethyldisilazide / 1.) THF, toluene, -78 deg C, 15 min, 2.) THF, toluene, -78 deg C, 30 min
4: 1N aq. NaOH / methanol / 16 h / Heating
5: K2CO3 / dimethylformamide / 1 h / 0 - 20 °C
6: 86 percent / dimedone, Pd(PPh3)4 / tetrahydrofuran / 16 h / Ambient temperature
7: toluene
8: potassium hexamethyldisilazide / tetrahydrofuran / 0.17 h / Ambient temperature
9: 100 percent / OsO4, N-methylmorpholine N-oxide / acetone; H2O / 24 h / Ambient temperature
10: 100 percent / NaIO4 / tetrahydrofuran; H2O / 1 h / Ambient temperature
11: toluene / 0.25 h
12: potassium hexamethyldisilazide / toluene; tetrahydrofuran / 0.17 h / Ambient temperature
With
sodium hydroxide; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium(0); potassium hexamethylsilazane; potassium carbonate; dimedone; 4-methylmorpholine N-oxide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ja00101a017