Multi-step reaction with 12 steps
1.1: dipyridinium dichromate / dichloromethane / 72 h / 20 °C / Molecular sieve
2.1: tetrahydrofuran / 0.5 h / -78 °C
2.2: 2 h / 20 °C
3.1: bromine / dichloromethane / 2 h / 20 °C
3.2: 0.33 h / 20 °C
3.3: 16 h / -78 - -30 °C
4.1: potassium carbonate / methanol / 12 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid / 1,2-dichloro-ethane / -30 - 20 °C / Reflux
6.1: sodium methylate / methanol / 0.25 h / -30 - 0 °C
7.1: toluene-4-sulfonic acid; 2,2-dimethoxy-propane / 13 h / 20 °C
8.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 h / 760.05 Torr
9.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C
10.1: sodium hydrogencarbonate; Selectfluor / acetonitrile / 1 h / 20 °C
11.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.08 h / -78 - 0 °C
11.2: 0.25 h / 0 °C
11.3: 0.5 h / 0 °C
12.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C
With
dipyridinium dichromate; palladium 10% on activated carbon; hydrogen; bromine; sodium methylate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; Selectfluor; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,2-dimethoxy-propane; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; toluene; acetonitrile;
DOI:10.1002/ejoc.201100062