Multi-step reaction with 12 steps
1: 1.) Me2LiCu*SMe2; 2.) 10percent KOH / 1.) Et2O, -30 deg C; 2.) EtOH, reflux, 40 min
2: dimethylformamide / 2 h / 130 °C
3: 0.17 h / 0 °C
4: 60 percent / 2.) MeOH / 2.) conc. HCl / 1.) Et2O, -78 deg C, 1 h; 2.) 25 deg C, 2 h
5: 1.) LDA, HMPA / tetrahydrofuran / 1.) -78 deg C; 2.) 25 deg C
6: LiAlH4 / diethyl ether / 0.25 h / 25 °C
7: 1.) KIO4, K2CO3, KMnO4; 2.) p-TsOH / 1.) aq. t-BuOH, 25 deg C, 60 h; 2.) C6H6, reflux, 20 min
8: 75 percent / CH3SO3H / CH2Cl2 / 46 h / Heating
9: 1.) BBr3; 2.) PDC / 1.) CH2Cl2, -78 deg C, 3 min; 2.) CH2Cl2, 25 deg C, 24 h
10: 37 percent / OsO4 / pyridine / 0.5 h / 25 °C
11: CF3CO3H / CH2Cl2 / 0.25 h / 0 °C
12: 76 percent / NaClO2, NH2SO2OH / dioxane; H2O / 0.5 h / 25 °C
With
methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium chlorite; potassium permanganate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; potassium metaperiodate; methanesulfonic acid; trifluoroacetyl peroxide; aminosulfonic acid; boron tribromide; potassium carbonate; Lithium dimethylcuprate-dimethyl sulfide complex; toluene-4-sulfonic acid; lithium diisopropyl amide;
hydrogenchloride;
In
tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00310a076