Multi-step reaction with 12 steps
1.1: camphor-10-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere
2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; toluene / 4 h / 20 °C / Inert atmosphere
3.1: sodium periodate / tetrahydrofuran; aq. phosphate buffer / 0.75 h / 0 °C / pH Ca. 7 / Inert atmosphere
4.1: sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere
5.1: triethylamine; dmap / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
6.1: sodium azide / N,N-dimethyl-formamide / 6 h / 80 °C / Inert atmosphere
7.1: acetic acid; water / 3 h / 100 °C / Inert atmosphere
8.1: triethylamine; dmap / dichloromethane / 5 h / 20 °C / Inert atmosphere
9.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
10.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
10.2: 36 h / Inert atmosphere; Reflux
11.1: tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
12.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h
With
dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium azide; palladium 10% on activated carbon; camphor-10-sulfonic acid; water; hydrogen; acetic acid; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; aq. phosphate buffer; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/j.tet.2013.12.078