Multi-step reaction with 19 steps
1.1: potassium hydroxide / ethanol / 4 h / Inert atmosphere; Reflux
1.2: 13 h / Reflux; Inert atmosphere
2.1: Oxone / methanol; water / 72 h / 20 - 60 °C
3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 24 h / -78 - 20 °C / Inert atmosphere
4.1: (DHQD)MEQ; potassium osmate(VI) dihydrate; potassium carbonate; potassium hexacyanoferrate(III); methanesulfonamide / water; tert-butyl alcohol / 30 h / 0 °C
5.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 5.5 h / 0 °C / Inert atmosphere
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 - 20 °C / Inert atmosphere
7.1: 1H-imidazole / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere
8.1: dmap / benzene / 17 h / 20 °C / Inert atmosphere
9.1: pyridinium p-toluenesulfonate / methanol / 0.75 h / 20 °C / Inert atmosphere
10.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 0.75 h / 20 °C / Molecular sieve; Inert atmosphere
11.1: sodium chlorite; sodium dihydrogen phosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 17 h / 20 °C
12.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 20 °C
13.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1.17 h / 20 °C
14.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 2.5 h / 20 °C / Molecular sieve
15.1: tetrakis(triphenylphosphine) palladium(0); phenylsilane / dichloromethane / 6 h / 20 °C
16.1: triethylamine; dmap; 2-methyl-6-nitrobenzoic anhydride / dichloromethane / 20.5 h / 20 °C
17.1: tetrakis(triphenylphosphine) palladium(0); phenylsilane / dichloromethane / 3.67 h / 20 °C
18.1: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 2 h / 20 °C
19.1: dmap; 2-methyl-6-nitrobenzoic anhydride / dichloromethane; tetrahydrofuran / 9 h / 20 °C
19.2: 39 h / 20 °C
With
pyridine; 1H-imidazole; dmap; potassium osmate(VI) dihydrate; Oxone; sodium chlorite; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium(0); tetrapropylammonium perruthennate; sodium dihydrogen phosphate; 2-methyl-but-2-ene; methanesulfonamide; phenylsilane; (DHQD)MEQ; 2-methyl-6-nitrobenzoic anhydride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; potassium carbonate; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hydroxide; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil; tert-butyl alcohol; benzene;
DOI:10.1021/acs.orglett.6b01235