Multi-step reaction with 12 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / Cooling with ice
2.1: acetic acid / water / 16 h / 20 °C
3.1: sodium periodate / 1,4-dioxane; water / 1 h
4.1: sodium hydroxide / water; tetrahydrofuran / 72 h / 20 °C / Cooling with ice
5.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C
5.2: 2 h / 20 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
6.2: 1 h / -78 °C / Cooling with ice
7.1: cerium(III) chloride / tetrahydrofuran / 1.58 h / 0 - 20 °C / Cooling with ice
7.2: 3 h / -78 °C
7.3: -78 - 20 °C
8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
8.2: 1 h / -78 °C / Cooling with ice
9.1: lithium borohydride; methanol / tetrahydrofuran / 2 h / -78 °C
10.1: dmap; triethylamine / dichloromethane / 2.5 h / 0 °C
11.1: sulfuric acid; acetic acid / 3 h / 20 °C
12.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.25 h / 40 °C
12.2: 2 h / Cooling with ice; Reflux
12.3: 16 h / 20 °C
With
methanol; dmap; sodium periodate; lithium borohydride; N,O-bis-(trimethylsilyl)-acetamide; cerium(III) chloride; oxalyl dichloride; sulfuric acid; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;
6.1: Swern Oxidation / 8.1: Swern Oxidation;