1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 3 h / 25 °C 2.1: sodium hydride / toluene / 1 h / 20 °C / Inert atmosphere 2.2: 4 h / 45 - 50 °C 2.3: 0 - 5 °C / pH 1 3.1: lithium chloride / dimethyl sulfoxide / 15 h / 150 - 160 °C 4.1: sodium hydroxide / ethylene glycol / 4 h / 170 - 180 °C 4.2: pH 1 5.1: di-isopropyl ether / 6 h / 20 - 75 °C 6.1: hydrogenchloride / water; tert-butyl methyl ether / 0.5 h / 20 - 25 °C 7.1: thionyl chloride / toluene / 3 h / 75 - 80 °C 8.1: sodium carbonate / toluene; water / 1 h / 0 - 5 °C 9.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 - 80 °C / Inert atmosphere 9.2: 0.5 h / 0 - 5 °C View Scheme

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 3 h / 25 °C 2.1: sodium hydride / toluene / 1 h / 20 °C / Inert atmosphere 2.2: 4 h / 45 - 50 °C 2.3: 0 - 5 °C / pH 1 3.1: lithium chloride / dimethyl sulfoxide / 15 h / 150 - 160 °C 4.1: sodium hydroxide / ethylene glycol / 4 h / 170 - 180 °C 4.2: pH 1 5.1: thionyl chloride / toluene / 3 h / 75 - 80 °C 6.1: sodium carbonate / toluene; water / 1 h / 0 - 5 °C 7.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 - 80 °C / Inert atmosphere 7.2: 0.5 h / 0 - 5 °C 8.1: hydrogen bromide / water / 3 h / 90 - 100 °C 9.1: (2S,3S)-(+)-di-O-benzoyl tartaric acid / isobutyl methylketone; methanol / 25 °C 9.2: pH 8 View Scheme