Multi-step reaction with 12 steps
1.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 0.75 h / 20 °C
2.1: tert.-butyl lithium; 9-methoxy-9-BBN / tetrahydrofuran; diethyl ether; hexane; pentane / 1.17 h / -78 - 20 °C
2.2: 50 °C
3.1: 2,3-Dimethyl-2-butene; dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C
3.2: 0 - 20 °C
4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0 - 20 °C / Molecular sieve
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 °C / pH 7 / aq. phosphate buffer
6.1: zinc trifluoromethanesulfonate / dichloromethane / 12 h / 20 °C
7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / -78 °C
7.2: -78 - 0 °C
8.1: 20% palladium hydroxide on charcoal; hydrogen / ethyl acetate / 20 °C
9.1: 1H-imidazole / dichloromethane / 7.5 h / 20 °C
10.1: 2,6-dimethylpyridine / dichloromethane / 1.67 h / -78 °C
11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -78 - 20 °C
12.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 9 h / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; osmium(VIII) oxide; tetrapropylammonium perruthennate; 2,3-Dimethyl-2-butene; dimethylsulfide borane complex; 20% palladium hydroxide on charcoal; hydrogen; iodine; tert.-butyl lithium; zinc trifluoromethanesulfonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 9-methoxy-9-BBN; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; tert-butyl alcohol; pentane;
2.2: Suzuki-Miyaura coupling;
DOI:10.1002/chem.201101437