Multi-step reaction with 9 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
1.2: -78 - 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran / -78 - -10 °C / Inert atmosphere
2.2: -78 - 20 °C / Inert atmosphere
3.1: 1H-imidazole / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere
4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere
4.2: Inert atmosphere
4.3: 19 h / Inert atmosphere; Reflux
5.1: hydrogen / ethyl acetate / 0.83 h / 5625.56 Torr / Inert atmosphere
6.1: methanol; water; sodium hydroxide / 21 h / 87 °C / Inert atmosphere
7.1: triphenylphosphine; diethylazodicarboxylate / toluene / 0 - 20 °C / Inert atmosphere
8.1: Jones reagent; potassium fluoride / acetone / 2 h / -10 °C / Inert atmosphere
9.1: chloroform-d1 / 96 h / Inert atmosphere
With
1H-imidazole; methanol; potassium fluoride; Jones reagent; n-butyllithium; oxalyl dichloride; water; hydrogen; dimethyl sulfoxide; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate;
In
tetrahydrofuran; chloroform-d1; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;
1.1: Swern oxidation / 1.2: Swern oxidation / 4.1: Suzuki Miyaura coupling / 4.2: Suzuki Miyaura coupling / 4.3: Suzuki Miyaura coupling / 7.1: Mitsunobu reaction;
DOI:10.1021/ml1001807