Multi-step reaction with 14 steps
1.1: dimethylsulfide; boron trifluoride diethyl etherate / 1 h / -20 °C
2.1: dmap; triethylamine / dichloromethane / 16 h / 35 °C
3.1: potassium carbonate / methanol / 3 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 35 °C
5.1: n-butyllithium; diethylaluminium chloride / toluene / 0.33 h / 0 °C
6.1: potassium carbonate / methanol / 2 h / 20 °C
7.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / 1 h / 20 °C
7.2: 18 h / 20 °C
8.1: Dess-Martin periodane / dichloromethane / 2 h / 30 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 50 °C
10.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 0 °C
11.1: methanol; acetyl chloride / tetrahydrofuran / 1 h / 0 °C
12.1: ammonia; hydroxylamine-O-sulfonic acid / methanol; dichloromethane / 10 h / 20 °C
12.2: 0.5 h / 0 °C
13.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -40 °C
14.1: toluene / 2 h / 60 °C
With
methanol; dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; dimethylsulfide; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonia; diethylaluminium chloride; potassium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; hydroxylamine-O-sulfonic acid;
In
tetrahydrofuran; methanol; dichloromethane; toluene;
7.1: Sonogashira coupling / 8.1: Dess-Martin oxidation / 10.1: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2011.03.149