Multi-step reaction with 11 steps
1.1: water; sodium periodate / tetrahydrofuran; diethyl ether / 2 h / 20 °C
2.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere
2.2: -78 - -40 °C / Inert atmosphere
2.3: 0.5 h / -40 °C / Inert atmosphere
3.1: dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere
4.1: water; acetic acid / tetrahydrofuran / 5 h / -20 °C
5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 12 h / 20 °C / Inert atmosphere
5.2: 19 h / 20 °C / Inert atmosphere
6.1: methanol; barium hydroxide octahydrate / 0.33 h / 20 °C
7.1: tetrapropylammonium perruthennate / dichloromethane / 0.5 h / 20 °C
7.2: 24 h / 20 °C
8.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; dichloromethane; toluene / 0.75 h / -20 °C / Inert atmosphere
9.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane; decane / 5 h / -20 °C / Molecular sieve; Inert atmosphere
10.1: tributylphosphine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere
11.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride; water / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 - 20 °C
With
titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; dmap; sodium periodate; tetrapropylammonium perruthennate; barium hydroxide octahydrate; tributylphosphine; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; acetic acid; triethylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; decane; dichloromethane; N,N-dimethyl-formamide; toluene;
9.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1021/jo3026077