Multi-step reaction with 18 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 25 °C / Inert atmosphere
2.1: 10-camphorsufonic acid / methanol / 3 h / 25 °C / Inert atmosphere
3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0 - 25 °C / Inert atmosphere; Molecular sieve
4.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere
4.2: -78 - 0 °C / Inert atmosphere
5.1: p-toluenesulfonic acid monohydrate / methanol; dichloromethane / 3 h / 25 °C / Inert atmosphere
6.1: 1H-imidazole / dichloromethane / 1 h / 25 °C / Inert atmosphere
7.1: bis(cyclohexanyl)borane / tetrahydrofuran / 0 - 25 °C / Inert atmosphere
7.2: 1 h / 0 °C / Inert atmosphere
8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 25 °C / Inert atmosphere
9.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 25 °C / Inert atmosphere
10.1: dmap; 2-methyl-6-nitrobenzoic anhydride; triethylamine / toluene / 0.33 h / 25 °C / Inert atmosphere; Molecular sieve
10.2: 13 h / 25 °C / Inert atmosphere; Molecular sieve
11.1: p-toluenesulfonic acid monohydrate / methanol; dichloromethane / 0.67 h / 0 °C / Inert atmosphere
12.1: N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride / tetrahydrofuran; dichloromethane / 0 - 25 °C / Inert atmosphere
12.2: 0.67 h / 25 °C / Inert atmosphere
13.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere
14.1: bis(cyclohexanyl)borane / tetrahydrofuran / 6 h / 25 °C / Inert atmosphere
14.2: 20 h / 0 °C / Inert atmosphere
15.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 - 25 °C / Inert atmosphere
16.1: p-toluenesulfonic acid monohydrate / methanol; dichloromethane / 0.5 h / 0 °C / Inert atmosphere
17.1: zinc trifluoromethanesulfonate / dichloromethane / 16 h / 25 °C / Inert atmosphere
18.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / -78 - 30 °C / Inert atmosphere
18.2: -78 - 0 °C / Inert atmosphere
With
1H-imidazole; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; N,N,N,N,-tetramethylethylenediamine; bis(cyclohexanyl)borane; 10-camphorsufonic acid; 2-methyl-6-nitrobenzoic anhydride; p-toluenesulfonic acid monohydrate; sodium hexamethyldisilazane; titanium tetrachloride; zinc trifluoromethanesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol;
4.1: Wittig reaction / 4.2: Wittig reaction / 7.1: Hydroboration reaction / 14.1: Hydroboration reaction;
DOI:10.1021/ja109533y