Multi-step reaction with 15 steps
1.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C
2.1: potassium carbonate / methanol / 19 h / 20 - 45 °C
3.1: triethylamine; dmap / dichloromethane / 1.5 h / 20 °C
4.1: copper(l) iodide / acetonitrile / 24 h / 20 °C
5.1: platinum(IV) oxide; hydrogen / ethyl acetate / 3 h / 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 22.5 h / 0 - 20 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / 0.25 h / -78 °C
7.2: 0.75 h / 0 °C
8.1: sodium hydride / tetrahydrofuran / 0 - 20 °C
9.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.17 h / -20 °C
10.1: 1H-imidazole; triethylamine; dmap / N,N-dimethyl-formamide
11.1: sodium hydroxide / methanol; water
12.1: triphenylphosphine / benzene / Reflux
13.1: acetic acid / tetrahydrofuran; water
14.1: Dess-Martin periodane / dichloromethane
15.1: silica gel / ethyl acetate; hexane
With
1H-imidazole; dmap; platinum(IV) oxide; sodium tetrahydroborate; copper(l) iodide; oxalyl dichloride; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; hydrogen; silica gel; sodium hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium hydroxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
7.2: |Swern Oxidation / 8.1: |Horner-Wadsworth-Emmons Olefination / 14.1: |Dess-Martin Oxidation;
DOI:10.1016/j.bmcl.2013.03.024