Multi-step reaction with 15 steps
1.1: 89 percent / sodium hydroxide; Adogen 464(R) / CH2Cl2 / 15 h / 20 °C
2.1: sodium borohydride / tetrahydrofuran; methanol / 2 h
3.1: imidazole / dimethylformamide / 12 h / 20 °C
4.1: n-butyllithium / 1 h / -78 °C
4.2: trimethyl borate / 12 h / -78 - 20 °C
4.3: 78 percent / hydrogen peroxide / 12 h / 20 °C
5.1: 75 percent / potassium carbonate / acetone / 12 h / Heating
6.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 0 °C
7.1: SOCl2 / benzene / 12 h / 20 °C
7.2: dimethylsulfoxide; benzene / 20 °C
8.1: 98 percent / sodium hydroxide / ethanol / 20 h / Heating
9.1: oxalyl chloride / benzene / 2 h / 20 °C
10.1: sodium hydroxide / H2O; CH2Cl2 / 1 h / 20 °C
11.1: B2H6*THF; BF3*Et2O / tetrahydrofuran / Heating
11.2: 98 percent / hydrochloric acid / H2O; tetrahydrofuran
12.1: 73 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 48 h / 0 °C
13.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 0 °C
14.1: Dess-Martin periodinane / 1 h
15.1: NaClO2; Na2HPO4; resorcinol / dimethylsulfoxide / 12 h / 20 °C
With
1H-imidazole; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; n-butyllithium; thionyl chloride; oxalyl dichloride; B2H6-THF; Adogen 464(R); boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium carbonate; Dess-Martin periodane; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; recorcinol;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; benzene;
10.1: Schotten-Baumann reaction / 14.1: Dess-Martin oxidation;
DOI:10.1021/ol0261635