Multi-step reaction with 13 steps
1.1: rhodium (II) octanoate dimer / hexane / 6 h / Inert atmosphere; Reflux
2.1: diisobutylaluminium hydride / n-heptane; dichloromethane / 0.25 h / -78 °C / Inert atmosphere
3.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -30 °C / Inert atmosphere
4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1.75 h / -78 - 0 °C / Inert atmosphere
4.2: 1.75 h / -78 - 0 °C / Inert atmosphere
5.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C / Inert atmosphere
6.1: oxalic acid / methanol; dichloromethane / 0.5 h / 20 °C / Inert atmosphere
7.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
8.1: 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; triethylamine / 5 h / 85 °C / Inert atmosphere
9.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
10.1: sodium methylate / methanol / 0.17 h / 65 °C / Inert atmosphere
11.1: sodium tetrahydroborate / methanol / 0.25 h / 0 - 20 °C / Inert atmosphere
12.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.08 h / 0 °C / Inert atmosphere
12.2: 0.33 h / 60 °C / Inert atmosphere
13.1: borane-THF / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere
13.2: 1 h / 20 °C / Inert atmosphere
With
sodium tetrahydroborate; n-butyllithium; borane-THF; rhodium (II) octanoate dimer; boron trifluoride diethyl etherate; sodium methylate; sodium hexamethyldisilazane; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; oxalic acid; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide; mineral oil;
5.1: Rubottom oxidation / 8.1: Stetter reaction / 9.1: Aldol condensation;
DOI:10.1002/asia.201101021