Multi-step reaction with 11 steps
1.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.25 h / 20 °C / Molecular sieve
2.1: tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere
3.1: water; toluene-4-sulfonic acid / tetrahydrofuran; water; acetonitrile / 2 h / 20 °C
4.1: mercury(II) perchlorate hexahydrate / dichloromethane; water; acetonitrile / 1 h / 4 °C
5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 2 h / 20 °C
5.2: 1 h / 50 °C
6.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C
7.1: 1H-imidazole / tetrahydrofuran / 1 h / 20 °C
8.1: sodium periodate; potassium permanganate / tert-butyl alcohol / 17 h / 20 °C / pH 7.2 / aq. phosphate buffer; Inert atmosphere
9.1: pyridine hydrogenfluoride / tetrahydrofuran / 6 h / 4 °C / aq. buffer
10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 3 h / 20 °C
10.2: 20 °C
11.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 0.33 h / 20 °C
With
1H-imidazole; potassium permanganate; sodium periodate; tetrapropylammonium perruthennate; mercury(II) perchlorate hexahydrate; 2,4,6-trichlorobenzoyl chloride; 20 % Pd(OH)2/C; water; hydrogen; toluene-4-sulfonic acid; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jm300566h