Multi-step reaction with 9 steps
1.1: sodium periodate; water / dichloromethane / 0 - 20 °C
2.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / 0 °C
2.2: 1.33 h / -80 - 0 °C
3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C
4.1: lithium borohydride / tetrahydrofuran; methanol / 19 h / 0 - 20 °C
5.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 1 h / 0 °C
6.2: 0 - 20 °C
7.1: 10% palladium on activated charcoal; hydrogen / ethyl acetate / 18 h / 20 °C
8.1: water; sodium hydroxide / ethanol / 0 - 20 °C
9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 0.5 h / 20 °C
9.2: 2 h
With
2,6-dimethylpyridine; sodium periodate; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; 10% palladium on activated charcoal; water; hydrogen; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; sodium hydroxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; toluene; acetonitrile;
5.1: Dess-Martin oxidation / 6.1: Wittig-Horner reaction / 6.2: Wittig-Horner reaction;
DOI:10.1055/s-0030-1259287