Multi-step reaction with 11 steps
1.1: Bu2SnO / toluene / 2 h / Heating
1.2: 92 percent / cesium fluoride / dimethylformamide / 10 h
2.1: LiBH4 / tetrahydrofuran / 4 h / 20 °C
2.2: 24.5 g / LiBH4 / tetrahydrofuran / 4 h / -78 °C
3.1: 97 percent / imidazole / CH2Cl2 / 0.5 h / 0 °C
4.1: 95 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 5 h
5.1: 96 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; aq. phosphate buffer / 2 h / pH 7
6.1: 81 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 20 °C
7.1: 91 percent / methanol / 0.67 h
8.1: 97 percent / Dess-Martin periodinane / CH2Cl2 / 2 h
9.1: 65 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran; CH2Cl2 / 0.08 h / -93 °C
10.1: 94 percent / imidazole / tetrahydrofuran / 48 h
11.1: 78 percent / [Rh2(OAc)4] bis(methanol) adduct / benzene / 0.42 h / 80 °C
With
1H-imidazole; dmap; lithium borohydride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; di(n-butyl)tin oxide; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
dirhodium tetraacetate;
In
tetrahydrofuran; methanol; phosphate buffer; dichloromethane; toluene; benzene;
8.1: Dess-Martin oxidation;
DOI:10.1002/chem.200601212