Multi-step reaction with 10 steps
1.1: methanol / 24 h / 60 °C
2.1: tert.-butyl lithium / tetrahydrofuran; n-heptane / 1 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 - 20 °C / Inert atmosphere
3.1: sodium acetate; palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / toluene / 23 h / 50 °C
4.1: triethylamine / 1.5 h / 20 °C
5.1: triethylamine; methanesulfonyl chloride / dichloromethane / 3 h / 0 °C
6.1: Ni(OAc)2-(H2O)4-(S,S)-N,N'-dibenzylcyclohexane-1,2-diamine complex / 1,2-dimethoxyethane / 0 °C
7.1: hydrogen / methanol / 2 h / 75 °C / 46544.6 Torr
8.1: hydrogen; palladium 10% on activated carbon / methanol / 1.5 h
9.1: thionyl chloride / 0 - 20 °C
10.1: triethylamine / dichloromethane / 0 - 20 °C
With
1,1'-bis-(diphenylphosphino)ferrocene; thionyl chloride; Ni(OAc)2-(H2O)4-(S,S)-N,N'-dibenzylcyclohexane-1,2-diamine complex; palladium 10% on activated carbon; hydrogen; tert.-butyl lithium; sodium acetate; palladium diacetate; methanesulfonyl chloride; triethylamine;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; n-heptane; dichloromethane; toluene;
4.1: |Henry Nitro Aldol Condensation;
DOI:10.1021/ol500529w