Multi-step reaction with 23 steps
1.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere
2.1: acetic acid; zinc / ethanol / 2 h / 23 °C / Inert atmosphere
3.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere
4.1: Proton Sponge.(R). / dichloromethane / 3 h / 23 °C / Inert atmosphere; Molecular sieve
5.1: hydrogenchloride / methanol / 0.25 h / 23 °C / Inert atmosphere
6.1: pyridine-SO3 complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 23 °C / Inert atmosphere
7.1: triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
7.2: 0 °C / Inert atmosphere
8.1: tetrakis(triphenylphosphine) palladium(0); thallium(I) carbonate / tetrahydrofuran; water / 10 h / 23 °C / Inert atmosphere; Darkness
9.1: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / toluene / 23 - 120 °C / Inert atmosphere
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 23 °C / Inert atmosphere
11.1: pyridine-SO3 complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 23 °C / Inert atmosphere
12.1: triethylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere
13.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 1 h / 23 °C / Inert atmosphere
14.1: 2,6-di-tert-butyl-4-methyl-phenol; N,N-diethylaniline / acetonitrile / 7 h / 95 °C / Inert atmosphere
15.1: titanium tetrachloride / dichloromethane / 0.03 h / -78 °C / Inert atmosphere; Molecular sieve
16.1: Martins sulfurane / benzene / 0.5 h / 23 °C / Inert atmosphere
17.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C / Inert atmosphere
17.2: -78 - -40 °C / Inert atmosphere
17.3: -78 - -10 °C / Inert atmosphere
18.1: sodium tetrahydroborate / ethanol / 0.5 h / 0 °C / Inert atmosphere
19.1: potassium carbonate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; water / 0 °C / Inert atmosphere
20.1: water; toluene-4-sulfonic acid / benzene / 23 °C / Inert atmosphere
21.1: trichlorophosphate / 0.5 h / 0 °C / Inert atmosphere
21.2: 0 - 23 °C / Inert atmosphere
22.1: silica gel; 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; acetonitrile / 6 h / 23 °C / Inert atmosphere
23.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 23 °C / Inert atmosphere
With
1H-imidazole; hydrogenchloride; dmap; sodium chlorite; sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; Hoveyda-Grubbs catalyst second generation; thallium(I) carbonate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; Martins sulfurane; pyridine-SO3 complex; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; water; silica gel; titanium tetrachloride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N,N-diethylaniline; 2,3-dicyano-5,6-dichloro-p-benzoquinone; N,N`-dimethylethylenediamine; zinc; trichlorophosphate;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene;
8.1: Suzuki coupling / 14.1: Diels-Alder reaction;
DOI:10.1021/ja903790y