Multi-step reaction with 14 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
1.2: 3 h / -78 - 20 °C
2.1: copper(l) iodide / tetrahydrofuran; diethyl ether / 0.17 h / -40 °C
2.2: 0.75 h / -40 °C
3.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C
4.1: tetrahydrofuran; diethyl ether / 0.5 h / -78 °C
5.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 20 °C
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
6.2: 1 h / 20 °C
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0 - 20 °C / pH 7 / aq. phosphate buffer
8.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C
9.1: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C
10.1: caesium carbonate / tetrahydrofuran; water / 0.25 h / 20 °C
10.2: 16.25 h / 50 °C
11.1: 2,3-Dimethyl-2-butene; dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C
11.2: 0 - 20 °C
12.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0 - 20 °C / pH 7 / aq. phosphate buffer
13.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C
14.1: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -78 °C
With
2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper(l) iodide; 2,3-Dimethyl-2-butene; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; potassium hexamethylsilazane; sodium hydride; caesium carbonate; Dess-Martin periodane; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; mineral oil;
10.1: Suzuki-Miyaura coupling / 10.2: Suzuki-Miyaura coupling;
DOI:10.1002/chem.201101437