Multi-step reaction with 11 steps
1.1: periodic acid dihydrate / ethyl acetate / 4 h / 20 °C / Inert atmosphere
2.1: CSA / methanol / 1 h / 20 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C / Inert atmosphere
4.1: disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 30 h / 20 °C / Inert atmosphere
5.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere
5.2: 10 h
6.1: ozone / dichloromethane / 1.5 h / -78 °C / Inert atmosphere
6.2: -78 - 20 °C / Inert atmosphere
7.1: ethylmagnesium bromide / tetrahydrofuran / 0.25 h / 20 °C / Cooling with ice; Inert atmosphere
7.2: 1 h / -20 - 20 °C / Inert atmosphere
8.1: pyridine / 12 h / 20 °C / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
10.1: sodium hydrogencarbonate; potassium permanganate; sodium periodate / tert-butyl alcohol; water / 0.5 h / 20 °C
11.1: potassium cyanide / ethanol / 1 h / 20 °C / Inert atmosphere
11.2: CSA / 12 h / 20 °C
With
potassium cyanide; potassium permanganate; sodium periodate; disodium hydrogenphosphate; periodic acid dihydrate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/jo302773f