Multi-step reaction with 12 steps
1.1: dmap; 1H-imidazole / N,N-dimethyl-formamide / 20 °C
2.1: lithium diisopropyl amide / tetrahydrofuran / -78 - 20 °C
3.1: triethylamine; 4-acetamidobenzenesulfonyl azide / acetonitrile / 16 h / 20 °C
4.1: dichloromethane / 2 h / 0 - 20 °C
5.1: triethylamine / dichloromethane / 0 - 20 °C / Molecular sieve
5.2: 12 h / 20 °C
6.1: dirhodium tetraacetate / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / Reflux
7.1: sodium tetrahydroborate / methanol / 3 h / -30 - 20 °C
8.1: iodine; [bis(acetoxy)iodo]benzene / dichloromethane / 1.5 h / 20 °C / Irradiation
9.1: hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C
10.1: dicyclohexyl-carbodiimide / chloroform / 1 h / 20 °C / Irradiation
11.1: diisobutylaluminium hydride / dichloromethane; hexane / 3 h / -78 °C
12.1: potassium hexamethylsilazane / toluene; 1,2-dimethoxyethane / 2 h / -55 - 20 °C
With
1H-imidazole; dmap; dirhodium tetraacetate; sodium tetrahydroborate; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; 4-acetamidobenzenesulfonyl azide; hydrogen; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; 5,5-dimethyl-1,3-cyclohexadiene; ethanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile;
8.1: |Suarez Lodo Functionalization / 10.1: |Barton Decarboxylation / 12.1: |Julia-Kocienski Olefination;
DOI:10.1016/j.tet.2013.03.104