Multi-step reaction with 10 steps
1.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / -78 °C / Inert atmosphere
1.2: -78 - 0 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 34 h / Inert atmosphere
3.1: lithium borohydride / diethyl ether; water / 1.16 h / 0 - 20 °C / Inert atmosphere
4.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 4.5 h / 20 °C / Inert atmosphere
5.1: benzene / 6.5 h / 80 °C / Inert atmosphere
6.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
7.1: lithium hydroxide hydrate / water; tetrahydrofuran / 2 h / 50 °C / Inert atmosphere
8.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 2 h / -20 °C / Inert atmosphere
8.2: 4 h / -20 - 20 °C / Inert atmosphere
9.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
9.2: 3.5 h / Inert atmosphere
10.1: lithium borohydride / diethyl ether; water / 1 h / 0 - 20 °C / Inert atmosphere
With
dmap; lithium borohydride; lithium hydroxide hydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; benzene;
1.1: |Evans Aldol Reaction / 5.1: |Wittig Olefination;
DOI:10.3987/COM-13-12905