1.1: potassium carbonate / dimethyl sulfoxide / 0.25 h / 25 °C 1.2: 1 h / 25 °C 2.1: tri-n-butyl-tin hydride / 2,2'-azo-bisisobutyronitrile / toluene / 10 h / Reflux 2.2: 20 °C 3.1: sodium hydroxide / ethylene glycol / 4 h / 170 - 180 °C 3.2: pH 1 4.1: di-isopropyl ether / 6 h / 20 - 75 °C 5.1: hydrogenchloride / water; tert-butyl methyl ether / 0.5 h / 20 - 25 °C 6.1: thionyl chloride / toluene / 3 h / 75 - 80 °C 7.1: sodium carbonate / toluene; water / 1 h / 0 - 5 °C 8.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 - 80 °C / Inert atmosphere 8.2: 0.5 h / 0 - 5 °C View Scheme

1.1: potassium carbonate / dimethyl sulfoxide / 0.25 h / 25 °C 1.2: 1 h / 25 °C 2.1: tri-n-butyl-tin hydride / 2,2'-azo-bisisobutyronitrile / toluene / 10 h / Reflux 2.2: 20 °C 3.1: sodium hydroxide / ethylene glycol / 4 h / 170 - 180 °C 3.2: pH 1 4.1: thionyl chloride / toluene / 3 h / 75 - 80 °C 5.1: sodium carbonate / toluene; water / 1 h / 0 - 5 °C 6.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 - 80 °C / Inert atmosphere 6.2: 0.5 h / 0 - 5 °C 7.1: hydrogen bromide / water / 3 h / 90 - 100 °C 8.1: (2S,3S)-(+)-di-O-benzoyl tartaric acid / isobutyl methylketone; methanol / 25 °C 8.2: pH 8 View Scheme