Multi-step reaction with 15 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C
1.2: 2 h
2.1: acetic acid / 16 h / 20 °C
3.1: sodium periodate / 1,4-dioxane / 1.5 h / 20 °C
4.1: sodium hydroxide / water; tetrahydrofuran / 48 h / 20 °C / Cooling with ice
5.1: triethylamine / 16 h / 0 - 20 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
6.2: 0.25 h / -78 °C
7.1: cerium(III) chloride / tetrahydrofuran / 1.58 h / Cooling with ice
7.2: 1.5 h / -78 °C
8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
8.2: 0.25 h / -78 °C
9.1: cerium(III) chloride / tetrahydrofuran / 1.75 h / Cooling with ice
9.2: 1.5 h / -78 °C
10.1: thionyl chloride; pyridine / 1 h / 60 °C
11.1: sulfuric acid / water / 1 h / 20 °C
12.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.25 h / 40 °C
12.2: 4 h / 0 - 70 °C
13.1: ammonia; methanol / 12 h
14.1: dichloromethane / 16 h / 20 °C
14.2: 0.25 h
15.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene; tetrachloromethane / 3 h / 20 - 50 °C
With
pyridine; methanol; sodium periodate; thionyl chloride; N,O-bis-(trimethylsilyl)-acetamide; cerium(III) chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); sulfuric acid; ammonia; tri-n-butyl-tin hydride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
6.1: Swern Oxidation / 6.2: Swern Oxidation / 8.1: Swern Oxidation / 8.2: Swern Oxidation;