Multi-step reaction with 15 steps
1.1: sodium periodate; sodium hydrogencarbonate / water; ethanol / 4 h / 20 °C / Inert atmosphere
2.1: sodium tetrahydroborate / methanol / 1.08 h / 0 - 20 °C / Inert atmosphere
3.1: triethylamine; dmap / dichloromethane / 0 °C / Inert atmosphere
4.1: 18-crown-6 ether / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere
5.1: sodium / methanol / 0.5 h / 0 - 20 °C / Inert atmosphere
6.1: triethylamine; dmap / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
6.2: 0.17 h / Inert atmosphere
7.1: 2 h / 70 °C / Inert atmosphere
8.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere
9.1: hydrogen; 10 wt% Pd(OH)2 on carbon / methanol / 1 h / 20 °C / 760.05 Torr / Inert atmosphere
10.1: sodium carbonate / ethyl acetate / 2 h / 20 °C / Inert atmosphere
11.1: chromium(VI) oxide; acetic anhydride; pyridine / dichloromethane / 1.25 h / 0 - 20 °C / Inert atmosphere
12.1: potassium tert-butylate / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
13.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane; hexane / 2 h / 20 °C / Inert atmosphere
14.1: trifluoroacetic acid / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere
15.1: sodium hydride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere
With
pyridine; chromium(VI) oxide; dmap; sodium tetrahydroborate; sodium periodate; 18-crown-6 ether; trifluorormethanesulfonic acid; 10 wt% Pd(OH)2 on carbon; potassium tert-butylate; hydrogen; sodium; acetic anhydride; sodium hydride; sodium hydrogencarbonate; sodium carbonate; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; cyclohexane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1039/c3ra47555g