Multi-step reaction with 13 steps
1.1: ozone / methanol; dichloromethane / -78 °C
1.2: -78 - 20 °C
2.1: 1H-imidazole; tert-butyldimethylsilyl chloride / dichloromethane / 20 °C
2.2: 20 °C
3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 20 °C
4.1: cerium(III) chloride / tetrahydrofuran / -78 °C
5.1: potassium carbonate / methanol; water / 50 °C
5.2: 0 °C
6.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / -78 °C
6.2: 65 °C
7.1: ammonium chloride; zinc / ethanol / 160 °C / Microwave irradiation
8.1: pyridinium p-toluenesulfonate / dichloromethane / 40 °C
9.1: N-Bromosuccinimide; sodium hydrogencarbonate; dibenzoyl peroxide / tetrachloromethane; benzene / 70 °C
9.2: 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
11.1: dmap; triethylamine / dichloromethane / 20 °C
12.1: toluene-4-sulfonic acid / methanol; N,N-dimethyl-formamide / 200 °C / Microwave irradiation
13.1: dmap / dichloromethane / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; cerium(III) chloride; trifluoromethylsulfonic anhydride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; tert-butyldimethylsilyl chloride; triethylamine; zinc; dibenzoyl peroxide;
In
tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1038/nchem.1074