Multi-step reaction with 8 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 0 - 22 °C / Inert atmosphere
2.1: bis-(1,2-dimethylpropyl)borane / 24 h / 0 - 22 °C / Inert atmosphere
2.2: 16 h / 22 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / 22 °C / Inert atmosphere
4.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; zinc trifluoromethanesulfonate; (R)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-5H-dibenz[b,f]azepine / 1,2-dichloro-ethane / 24 h / 22 °C / Inert atmosphere
4.2: 2.5 h / 0 - 22 °C / Inert atmosphere
5.1: ozone; triphenylphosphine / dichloromethane / 4 h / -78 - 22 °C / Inert atmosphere
6.1: potassium tert-butylate / tert-butyl alcohol / 0.25 h / 22 °C / Inert atmosphere
7.1: hydrazine hydrate / diethylene glycol / 2 h / 22 - 160 °C / Inert atmosphere
7.2: 4 h / 22 - 180 °C / Inert atmosphere
8.1: sodium periodate; ruthenium(III) chloride trihydrate / acetonitrile; tetrachloromethane / 2 h / 22 °C / Inert atmosphere
With
1H-imidazole; sodium periodate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-5H-dibenz[b,f]azepine; ruthenium(III) chloride trihydrate; potassium tert-butylate; tetrabutyl ammonium fluoride; bis-(1,2-dimethylpropyl)borane; zinc trifluoromethanesulfonate; ozone; hydrazine hydrate; triphenylphosphine;
In
tetrahydrofuran; tetrachloromethane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; diethylene glycol;
7.1: |Wolff-Kishner-Huang Minlon Reduction;
DOI:10.1021/ja503972p