Multi-step reaction with 10 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 2 h / -78 °C
2.1: 1,3-dimethylbarbituric acid; palladium diacetate; triphenylphosphine / ethanol / 2 h / 20 °C
3.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C
4.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water; toluene / 2 h / 20 °C
5.1: Celite-supported silver carbonate / toluene / 2 h / 130 °C / Darkness
6.1: n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran / 1 h / -78 °C
6.2: 4 h / -78 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 20 °C
8.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.08 h / 0 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 1 h / Reflux
10.1: toluene-4-sulfonic acid / toluene / 0.25 h / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; triethylsilane; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; 1,3-dimethylbarbituric acid; boron trifluoride diethyl etherate; palladium diacetate; toluene-4-sulfonic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo2021696