Multi-step reaction with 11 steps
1.1: potassium osmate; K3Fe(CN)6; (DHQD)2PHAL; methanesulfonamide; potassium carbonate / water; tert-butyl alcohol / 36 h / 0 °C
2.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere
3.2: 0.5 h / -78 °C / Inert atmosphere
4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 2 h / -78 - -45 °C / Inert atmosphere
4.2: 2 h / -78 °C / Inert atmosphere
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / -45 °C / Inert atmosphere
6.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
7.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 48 h / 20 °C / Inert atmosphere
8.1: palladium 10% on activated carbon; hydrogen / ethanol
9.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
9.2: -78 - 20 °C / Inert atmosphere
10.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / 0 °C / Inert atmosphere
10.2: -78 - 0 °C / Inert atmosphere
11.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
With
1H-imidazole; 2,6-dimethylpyridine; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; potassium osmate; methanesulfonamide; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; K3Fe(CN)6; (DHQD)2PHAL; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
1.1: Sharpless dihydroxylation / 9.1: Swern oxidation / 9.2: Swern oxidation;
DOI:10.1021/ml200254h