Multi-step reaction with 7 steps
1.1: 1H-imidazole / tetrahydrofuran / 1.5 h / 20 °C
2.1: osmium(VIII) oxide; potassium hexacyanoferrate(III); (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); potassium carbonate / water / 15 h / 0 °C
3.1: 1H-imidazole / tetrahydrofuran / 4 h / 0 - 20 °C
4.1: camphor-10-sulfonic acid / methanol / 0.67 h / 0 °C
5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 7.5 h / 20 °C
5.2: 2.5 h
6.1: 1H-imidazole / dichloromethane / 3.5 h / 20 °C
7.1: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.42 h / -78 °C
7.2: 0.5 h / -78 °C
With
1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); [bis(acetoxy)iodo]benzene; potassium hexacyanoferrate(III); camphor-10-sulfonic acid; potassium hexamethylsilazane; potassium carbonate;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1021/ol301278e