Multi-step reaction with 16 steps
1: potassium hexamethylsilazane / 1,2-dimethoxyethane / -78 °C
2: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine / methanol / 1 h / Inert atmosphere; Reflux
3: potassium trimethylsilonate / tetrahydrofuran; diethyl ether / 13 h / 45 °C
4: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 0 °C
5: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 0 °C
6: dmap; triethylamine / dichloromethane / 4 h / 20 °C
7: tetrahydrofuran / 12 h / -40 °C
8: lithium diisopropyl amide / tetrahydrofuran / 0.33 h / -78 °C
9: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.33 h
10: methanol; potassium carbonate / 0.33 h / 20 °C
11: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C
12: dmap; triethylamine / dichloromethane / 10 h / 20 °C
13: water; acetic acid / tetrahydrofuran / 1 h / 0 °C
14: Dess-Martin periodane / dichloromethane / 0.17 h / 20 °C
15: tin(ll) chloride / dichloromethane / 24 h / 20 °C
16: tetrakis(triphenylphosphine) palladium(0) / ethanol / 5 h / 80 °C
With
methanol; dmap; tetrakis(triphenylphosphine) palladium(0); potassium trimethylsilonate; water; palladium diacetate; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; 3-chloro-benzenecarboperoxoic acid; tris-(o-tolyl)phosphine; tin(ll) chloride; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane;
1: Horner-Wadsworth-Emmons olefination / 2: Mizoroki-Heck cyclization / 9: Rubottom oxidation / 14: Dess-Martin oxidation;
DOI:10.1021/ol103024z