Multi-step reaction with 10 steps
1.1: toluene / 36 h / Reflux
2.1: lithium aluminium tetrahydride / diethyl ether / 0.17 h / 0 °C / Inert atmosphere
3.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / Inert atmosphere
4.1: potassium osmate(VI) dihydrate; methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 36 h / 0 °C
5.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
6.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 0 - 20 °C / Inert atmosphere
7.1: palladium 10% on activated carbon; hydrogen / ethanol
8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
8.2: -78 - 20 °C
9.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere
10.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
With
1H-imidazole; 2,6-dimethylpyridine; potassium osmate(VI) dihydrate; lithium aluminium tetrahydride; oxalyl dichloride; methanesulfonamide; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium hexacyanoferrate(III);
In
diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
1.1: Johnson-Claisen orthoester rearrangement / 4.1: Sharpless dihydroxylation / 8.1: Swern oxidation / 8.2: Swern oxidation / 9.1: Evans aldol reaction;
DOI:10.1021/ml1002184