Multi-step reaction with 9 steps
1.1: 41 percent / K2CO3 / dimethylformamide / 20 - 80 °C
2.1: BBr3 / CH2Cl2 / -15 - 20 °C
2.2: 76 percent / SOCl2 / methanol / 20 - 70 °C
3.1: K2CO3 / dimethylformamide / 36 h / 20 °C
4.1: 1 N NaOH / dioxane; methanol / 20 °C
5.1: Et3N / tetrahydrofuran / 0.42 h / -20 - -15 °C
5.2: NaBH4 / tetrahydrofuran; methanol / 0 °C
6.1: dicyclohexylcarbodiimide; 1 M H3PO4 / dimethylsulfoxide / 2 h / 20 °C
7.1: tetrahydrofuran / 12 h / 20 °C
8.1: Ph3P; diethyl azodicarboxylate / tetrahydrofuran / 14 h / 20 °C
9.1: hydrazine hydrate / ethanol; CH2Cl2 / 0.5 h / Heating
With
sodium hydroxide; phosphoric acid; boron tribromide; potassium carbonate; hydrazine hydrate; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
1.1: Condensation / 2.1: deprotection / 2.2: deprotection / 3.1: Alkylation / 4.1: Hydrolysis / 5.1: Condensation / 5.2: Reduction / 6.1: Oxidation / 7.1: Addition / 8.1: Mitsunobu reaction / 9.1: Substitution;
DOI:10.1021/jm9904102