Multi-step reaction with 10 steps
1.1: bis-triphenylphosphine-palladium(II) chloride; N-ethyl-N,N-diisopropylamine / toluene / 0.33 h / 190 °C / Microwave irradiation; Inert atmosphere
2.1: 10 wt% Pd(OH)2 on carbon; hydrogen / isopropyl alcohol / 5 h / 20 °C
2.2: 15 h / 20 °C / Inert atmosphere
3.1: tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium / toluene; dichloromethane; decane / 2 h / 0 °C / Inert atmosphere; Molecular sieve
4.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere
5.1: hydrogen / ethanol / 3 h / Reflux; Inert atmosphere
6.1: triethylamine; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere
7.1: bismuth(lll) trifluoromethanesulfonate / diethyl ether / 2 h / 0 °C / Inert atmosphere
8.1: indium; aluminium / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
8.2: 3 h / -30 °C / Inert atmosphere
9.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 50 °C / Inert atmosphere
9.2: 1 h / 50 °C / Inert atmosphere
10.1: Amberlyst? 15 / toluene / 9 h / 50 °C / Inert atmosphere
With
bismuth(lll) trifluoromethanesulfonate; tert.-butylhydroperoxide; dmap; bis-triphenylphosphine-palladium(II) chloride; indium; bis(acetylacetonate)oxovanadium; 10 wt% Pd(OH)2 on carbon; hydrogen; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; aluminium;
In
tetrahydrofuran; diethyl ether; decane; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
1.1: |Diels-Alder Cycloaddition;
DOI:10.1021/ol400628h