Multi-step reaction with 16 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C
2.1: 1H-imidazole / dichloromethane / 2 h / 0 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C
3.2: 0.5 h / -78 °C
4.1: potassium hexamethylsilazane / 1,2-dimethoxyethane / -78 °C
5.1: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine / methanol / 1 h / Inert atmosphere; Reflux
6.1: potassium trimethylsilonate / tetrahydrofuran; diethyl ether / 13 h / 45 °C
7.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 0 °C
8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 0 °C
9.1: dmap; triethylamine / dichloromethane / 4 h / 20 °C
10.1: tetrahydrofuran / 12 h / -40 °C
11.1: lithium diisopropyl amide / tetrahydrofuran / 0.33 h / -78 °C
12.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.33 h
13.1: methanol; potassium carbonate / 0.33 h / 20 °C
14.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C
15.1: dmap; triethylamine / dichloromethane / 10 h / 20 °C
16.1: water; acetic acid / tetrahydrofuran / 1 h / 0 °C
With
1H-imidazole; methanol; dmap; lithium aluminium tetrahydride; oxalyl dichloride; potassium trimethylsilonate; water; palladium diacetate; potassium hexamethylsilazane; potassium carbonate; acetic acid; dimethyl sulfoxide; 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; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane;
3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Horner-Wadsworth-Emmons olefination / 5.1: Mizoroki-Heck cyclization / 12.1: Rubottom oxidation;
DOI:10.1021/ol103024z