Multi-step reaction with 11 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 °C
2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 2 h / -78 °C / Inert atmosphere
2.2: 2 h / -78 °C / Inert atmosphere
3.1: ammonium chloride / tetrahydrofuran / -78 - 30 °C / Inert atmosphere
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C
4.2: 12 h / 20 °C
5.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide; sodium periodate / diethyl ether; water / 24 h / 20 °C
6.1: triethylamine / 15 h / 20 °C
6.2: 2 h / -78 °C / Inert atmosphere
7.1: trifluoroacetic acid / dichloromethane; water / 18 h / 0 - 20 °C
8.1: L-proline / methanol / 25 °C
9.1: pyridinium p-toluenesulfonate / toluene / Reflux
10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 0 - 20 °C
11.1: diisopropyl-carbodiimide; dmap / dichloromethane / 24 h / 20 °C
With
dmap; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; ammonium chloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; diisopropyl-carbodiimide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;
2.2: |Swern Oxidation / 6.2: |Henry Nitro Aldol Condensation / 8.1: |Michael Addition;
DOI:10.1016/j.tet.2013.02.078