Multi-step reaction with 13 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: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / Reflux; Inert atmosphere
9.1: dmap; triethylamine / dichloromethane / 4 h / 0 °C / Inert atmosphere
10.1: (1,1';3',1''-terphenyl)-2'-ol; trimethylaluminum / hexane; toluene / 0.33 h / -78 °C / Inert atmosphere
10.2: 0.5 h / -78 °C / Inert atmosphere
11.1: 2,6-dimethylpyridine / dichloromethane / 0.33 h / 0 - 20 °C / Inert atmosphere
12.1: osmium(VIII) oxide; AD-mix β; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / water; tert-butyl alcohol / 48 h / 0 °C / Inert atmosphere
13.1: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 0 °C / Inert atmosphere
13.2: 1 h / 20 °C / Inert atmosphere
With
1H-imidazole; 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; borane-THF; methanesulfonamide; di-n-butylboryl trifluoromethanesulfonate; AD-mix β; (1,1';3',1''-terphenyl)-2'-ol; trimethylaluminum; diisobutylaluminium hydride; lithium dicyclohexylamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;
5.1: Aldol reaction / 5.2: Aldol reaction;
DOI:10.1021/ol202966m