Multi-step reaction with 10 steps
1: pyridine / dichloromethane; toluene / -78 - 0 °C
2: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -78 - 0 °C
3: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; toluene / 5 h
4: sodium periodate / acetone; toluene / 0.5 h
5: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol
6: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane
7: 1,4-diaza-bicyclo[2.2.2]octane; sodium periodate / tetrahydrofuran; water / 0.17 h
8: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane
9: trifluoroacetic acid / dichloromethane
10: palladium 10% on activated carbon; hydrogen / methanol / 24 h
With
pyridine; 1,4-diaza-bicyclo[2.2.2]octane; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; palladium 10% on activated carbon; boron trifluoride diethyl etherate; water; hydrogen; benzotriazol-1-ol; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
5: Pinnick oxidation;
DOI:10.1021/ol202573s