Multi-step reaction with 9 steps
1.1: trichlorophosphate / Reflux
2.1: sodium methylate
3.1: lithium diisopropyl amide / tetrahydrofuran / -55 °C
4.1: dmap / acetonitrile
5.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene
6.1: acetyl chloride / 20 °C / Reflux
6.2: 20 °C
7.1: ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane / 1 h / Inert atmosphere; Reflux
7.2: 20 °C
8.1: boron trichloride / dichloromethane / 1 h / -70 °C / Inert atmosphere
8.2: Inert atmosphere
9.1: dmap; triethylamine / N,N-dimethyl-formamide / 0 °C
9.2: 20 °C
With
dmap; ammonium sulfate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; boron trichloride; triethylamine; acetyl chloride; 1,1,1,3,3,3-hexamethyl-disilazane; lithium diisopropyl amide; trichlorophosphate;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
5.1: Barton-McCombie deoxygenation;
DOI:10.3390/molecules16065113