Multi-step reaction with 14 steps
1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water / 20 °C
1.2: 20 °C
2.1: magnesium bromide diethyl etherate / dichloromethane / 0 °C
3.1: 2,6-dimethylpyridine / dichloromethane / 0 °C
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 20 °C / pH 7 / aq. buffer
5.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 35 °C
6.1: potassium tert-butylate / tetrahydrofuran / 0 °C
7.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / -60 - -25 °C
8.1: 10% palladium on activated charcoal; hydrogen / ethyl acetate / 20 °C
9.1: Dess-Martin periodane / dichloromethane / 20 °C
10.1: lithium hexamethyldisilazane / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 6 h / -78 - 20 °C
11.1: potassium hydroxide / tetrahydrofuran; methanol / 60 °C
12.1: Dess-Martin periodane / dichloromethane / 20 °C
13.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 20 °C
14.1: methanol / benzene / 20 °C
With
2,6-dimethylpyridine; methanol; triethylsilane; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; Hoveyda-Grubbs catalyst second generation; magnesium bromide diethyl etherate; 2-methyl-but-2-ene; 10% palladium on activated charcoal; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; Dess-Martin periodane; 4-methylmorpholine N-oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; ethyl acetate; tert-butyl alcohol; benzene;
10.1: Julia Olefin synthesis;
DOI:10.1002/chem.201003135