Multi-step reaction with 7 steps
1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C
2.1: Burgess Reagent / benzene / 5 h / Reflux; Inert atmosphere
3.1: sodium hypochlorite; disodium hydrogenphosphate / (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III) / dichloromethane / 21 h / 0 - 20 °C / Reflux
4.1: hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 760.05 Torr
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -55 - -50 °C
5.2: 0.5 h / -50 - -20 °C
6.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -65 - -60 °C / Inert atmosphere
6.2: 1.5 h / -78 - 20 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 50 °C
With
methanol; sodium hypochlorite; sodium tetrahydroborate; disodium hydrogenphosphate; n-butyllithium; oxalyl dichloride; Burgess Reagent; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide;
(-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
5.1: Swern Oxidation / 5.2: Swern Oxidation;