Multi-step reaction with 13 steps
1.1: hydrogenchloride; water / methanol / 12 h / 30 °C
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C
2.2: Claisen-Schmidt Condensation / 12.67 h / 2 - 20 °C
3.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.55 h / 0 °C
3.2: 0.33 h / 20 °C
3.3: 0.75 h / -10 °C
4.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C
5.1: hydroquinidein 1,4-phthalazinediyl diether; methanesulfonamide / tert-butyl alcohol; water / 0 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C
7.1: pyridinium p-toluenesulfonate; orthoformic acid triethyl ester / 1,2-dichloro-ethane / 5.33 h / 20 - 50 °C
7.2: 20 °C
8.1: N-iodo-succinimide / N,N-dimethyl-formamide / 0 °C
9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 - 20 °C
10.1: hydrogenchloride; water / methanol / 3 h / 50 °C
11.1: potassium phosphate / acetonitrile / 75 °C
12.1: palladium diacetate; triphenylphosphine; silver carbonate / acetonitrile / 15 h / 115 °C / Inert atmosphere
13.1: boron tribromide / dichloromethane / 10 h / -78 - 40 °C / Inert atmosphere
With
1H-imidazole; hydrogenchloride; potassium phosphate; N-iodo-succinimide; methanesulfonamide; tetrabutyl ammonium fluoride; water; palladium diacetate; pyridinium p-toluenesulfonate; chloroformic acid ethyl ester; boron tribromide; sodium hydride; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; orthoformic acid triethyl ester; triphenylphosphine; silver carbonate;
In
tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; mineral oil; tert-butyl alcohol;
2.1: |Claisen-Schmidt Condensation / 5.1: |Sharpless Dihydroxylation / 12.1: |Heck Reaction;
DOI:10.1021/ol4021095