Multi-step reaction with 17 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 °C / Inert atmosphere
2.1: 4-methyl-morpholine / dichloromethane / 1 h / 20 °C / Inert atmosphere
3.1: methyl iodide; sodium hydrogencarbonate / acetonitrile; water / 21 h / 20 °C
4.1: samarium diiodide / tetrahydrofuran; methanol / 0.5 h / -20 °C / Inert atmosphere
5.1: lithium borohydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
6.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.33 h / 0 °C / Inert atmosphere
6.2: 1 h / 0 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
8.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 0 °C / Inert atmosphere
9.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -78 °C / Inert atmosphere
9.2: 0.25 h / -78 °C / Inert atmosphere
10.1: diethyl ether / 0.33 h / -80 °C / Inert atmosphere
11.1: hydrogenchloride / methanol / 21 h / 20 °C
12.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -80 °C / Inert atmosphere
13.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -80 - 0 °C / Inert atmosphere
14.1: n-butyllithium / tetrahydrofuran; hexane; N,N,N,N,N,N-hexamethylphosphoric triamide / 0.67 h / -100 °C / Inert atmosphere
15.1: toluene-4-sulfonic acid / dichloromethane; methanol / 0.5 h / 20 °C
16.1: lithium bromide; magnesium bromide diethyl etherate / dichloromethane / 3 h / -15 - 0 °C / Inert atmosphere
17.1: sodium hydroxide; 18-crown-6 ether / tetrahydrofuran; water / 8 h / 0 °C
With
4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; lithium borohydride; n-butyllithium; samarium diiodide; magnesium bromide diethyl etherate; oxalyl dichloride; 18-crown-6 ether; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; lithium bromide; sodium hydroxide; methyl iodide;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
2.1: |Michael Addition / 17.1: |Favorskii Rearrangement;
DOI:10.1021/ol500788c