Multi-step reaction with 11 steps
1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 9 h / 20 °C / Inert atmosphere
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -60 °C
2.2: -60 - 20 °C
3.1: titanium(IV) trichloride isopropoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere
3.2: -78 °C / Inert atmosphere
4.1: trifluorormethanesulfonic acid / diethyl ether / 1.75 h / -20 - 20 °C
5.1: tert.-butyl lithium / diethyl ether; pentane / 0.58 h / -78 °C / Inert atmosphere
5.2: 1.5 h / -78 °C / Inert atmosphere
6.1: C17H34N4OS; acetic acid / toluene / 110 h / 20 - 45 °C / Inert atmosphere
7.1: pyridine hydrogenfluoride / tetrahydrofuran / 16 h / 0 - 20 °C
8.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C
9.1: piperidine; toluene-4-sulfonic acid / toluene / Inert atmosphere
10.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol; water; acetone / 1.5 h
11.1: ethyl acetate; diethyl ether; ethanol
With
piperidine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; titanium(IV) trichloride isopropoxide; trifluorormethanesulfonic acid; palladium 10% on activated carbon; C17H34N4OS; hydrogen; tert.-butyl lithium; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetone; toluene; tert-butyl alcohol; pentane;
2.1: |Swern Oxidation / 2.2: |Swern Oxidation;
DOI:10.1021/ol400046n