Multi-step reaction with 13 steps
1.1: N,N-dimethyl-formamide / 8 h / Reflux
2.1: water; sodium hydroxide / ethanol / 12 h / 20 °C
3.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 14 h / 70 °C
4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere
4.2: -78 - 20 °C / Inert atmosphere
5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere
5.2: Inert atmosphere; Reflux
6.1: ozone / dichloromethane / 1 h / -78 °C
7.1: pyridinium p-toluenesulfonate / ethanol / 6 h / 50 °C
8.1: water; dihydrogen peroxide; sodium hydroxide / dimethyl sulfoxide / 4 h / 20 °C
9.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C
10.1: manganese(IV) oxide / dichloromethane / 48 h / Reflux
11.1: toluene / Reflux
12.1: sodium tetrahydroborate; bismuth(III) chloride / ethanol / 20 °C / Cooling with ice
13.1: copper(l) iodide; potassium carbonate; L-proline / dimethyl sulfoxide / 24 h / 130 °C / Molecular sieve
With
manganese(IV) oxide; bismuth(III) chloride; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; thionyl chloride; water; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; diisopropylamine; N,N-dimethyl-formamide; L-proline; sodium hydroxide;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;
11.1: Wittig reaction;
DOI:10.1016/j.bmcl.2011.04.086