Multi-step reaction with 9 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
1.2: 21.5 h / 0 - 20 °C
2.1: sodium hydrogencarbonate; methyl iodide / acetonitrile; water / 19 h / 20 °C
3.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / tetrahydrofuran; water; tert-butyl alcohol / 0.5 h / 4 °C
4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 3 h / 20 °C
4.2: 1.5 h / 50 °C
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C
6.1: 1H-imidazole / tetrahydrofuran / 4 h / 20 °C
7.1: sodium periodate; potassium permanganate / tert-butyl alcohol; aq. phosphate buffer / 0.13 h / 20 °C / pH 7.2 / Inert atmosphere
8.1: pyridine hydrogenfluoride / tetrahydrofuran / 22 h / 4 °C / Cooling
9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 3 h / 20 °C
9.2: 3.5 h / 20 °C
With
1H-imidazole; sodium chlorite; potassium permanganate; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; sodium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl iodide;
In
tetrahydrofuran; aq. phosphate buffer; dichloromethane; water; toluene; acetonitrile; mineral oil; tert-butyl alcohol;
4.1: |Yamaguchi Lactonization / 4.2: |Yamaguchi Lactonization / 9.1: |Yamaguchi Lactonization / 9.2: |Yamaguchi Lactonization;
DOI:10.1016/j.tet.2013.02.008