Multi-step reaction with 11 steps
1.1: borane-THF / tetrahydrofuran / 48 h / 0 - 20 °C / Inert atmosphere
2.1: 1H-imidazole; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
3.1: lithium dicyclohexylamide / toluene / 0.17 h / 0 °C / Inert atmosphere
3.2: 20 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / diethyl ether / 1 h / -78 °C / Inert atmosphere
5.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / diethyl ether / 0.55 h / -100 °C / Inert atmosphere
5.2: 7 h / -100 - -78 °C / Inert atmosphere
6.1: tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 20 h / -20 °C / Inert atmosphere
7.1: dmap; triethylamine / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere
8.1: N,N,N,N,N,N-hexamethylphosphoric triamide / Inert atmosphere
9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / Inert atmosphere
10.1: dmap / Inert atmosphere
11.1: (1,1';3',1''-terphenyl)-2'-ol; trimethylaluminum / hexane; toluene / -48 °C / Inert atmosphere
11.2: -48 °C / Inert atmosphere
With
1H-imidazole; dmap; borane-THF; di-n-butylboryl trifluoromethanesulfonate; (1,1';3',1''-terphenyl)-2'-ol; trimethylaluminum; diisobutylaluminium hydride; lithium dicyclohexylamide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile;
5.1: Aldol reaction / 5.2: Aldol reaction / 11.1: Aldol reaction / 11.2: Aldol reaction;
DOI:10.1021/ol202966m