Multi-step reaction with 13 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran; toluene / 0.17 h / 0 - 20 °C / Inert atmosphere
1.2: 0.67 h / 20 °C / Inert atmosphere
2.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
3.1: sodium periodate; sodium hydrogencarbonate / dichloromethane; water / 20 °C / Inert atmosphere
4.1: sodium tetrahydroborate / methanol / 0.17 h / 0 °C / Inert atmosphere
5.1: Crabtree's catalyst; hydrogen / dichloromethane / 0 °C / Inert atmosphere
6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere
7.1: chromium dichloride; manganese; zirconocene dichloride; N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; lithium chloride / acetonitrile / 4 h / 20 °C / Inert atmosphere
8.1: triethylsilane; triethylsilyl trifluoromethyl sulfonate / acetonitrile / 0.33 h / -40 °C / Inert atmosphere
9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere
10.1: chromium dichloride; manganese; zirconocene dichloride; C26H32Cl2N2O4S; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; lithium chloride / acetonitrile / 3 h / 20 °C / Inert atmosphere
11.1: 18-crown-6 ether; potassium hydride / toluene / 24 h / 0 - 20 °C / Inert atmosphere
12.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C / Inert atmosphere
13.1: pyridine; silver nitrate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
With
pyridine; chromium dichloride; triethylsilane; manganese; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; zirconocene dichloride; Crabtree's catalyst; 18-crown-6 ether; N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; C26H32Cl2N2O4S; water; hydrogen; triethylsilyl trifluoromethyl sulfonate; potassium hydride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; silver nitrate; 4-methylmorpholine N-oxide; lithium chloride; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ol300672q