Multi-step reaction with 14 steps
1.1: camphorsulfonic acid / methanol / 16 h / Reflux; Inert atmosphere
2.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere
3.1: silica gel-supported NaIO4 / methanol; dichloromethane / 3 h / 20 °C / Inert atmosphere
4.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
4.2: 3.5 h / 0 - 20 °C / Inert atmosphere
5.1: 1H-imidazole; sodium hydrogencarbonate / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
6.1: dmap; triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
7.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
7.2: 1 h / -78 - 0 °C / Inert atmosphere
8.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.25 h / 0 °C / Inert atmosphere
9.1: triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid / toluene / 15 h / 20 °C / Inert atmosphere
9.2: 2 h / 20 °C / Inert atmosphere
10.1: trifluoroacetic acid / dichloromethane; water / 0.17 h / 20 °C / Inert atmosphere
11.1: N-ethyl-N,N-diisopropylamine; sodium iodide / tetrahydrofuran / 4.5 h / 20 °C / Reflux; Inert atmosphere
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
13.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 19 h / 20 °C / Inert atmosphere
14.1: potassium hexamethylsilazane / toluene / 2 h / -78 °C / Inert atmosphere
14.2: 20.5 h / -78 - 85 °C / Inert atmosphere
With
1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; sodium iodide; lithium hexamethyldisilazane; diethylazodicarboxylate; 4-nitro-benzoic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene;
5.1: Baylis-Hillman reaction / 8.1: Luche reduction / 9.2: Mitsunobu reaction / 14.1: Ireland-Claisen rearrangement / 14.2: Ireland-Claisen rearrangement;
DOI:10.1039/c1cc11388g