Multi-step reaction with 10 steps
1.1: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 1 h / -78 °C
2.3: 4 h / Reflux
3.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Reflux
5.1: hydrogenchloride; water; acetic acid / 1 h / Reflux
6.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 0.5 h / 20 °C
7.1: tetrahydrofuran / 20 °C
8.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 2 h / 20 °C
9.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 0.5 h / 20 °C
10.1: N'-methyl-N'-nitro-N-nitrosoguanidine / diethyl ether / 2 h / 20 °C
10.2: 2 h / Reflux
With
hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; water; boron tribromide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N,N-dimethyl-formamide; N'-methyl-N'-nitro-N-nitrosoguanidine;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1248/cpb.59.1369