1: 1. diisopropylamine, 1.4 M BuLi in hexane / 1.) 0-5 deg C, 10 min then ambient temperature, 18 h 2.) DMF, room temperature, 3 days 2: NaHCO3 / dimethylformamide / 72 h / Ambient temperature 3: 53 percent / 1N hydrochloric acid / tetrahydrofuran / 15 h / 40 °C View Scheme

1: 56 percent / tetrahydrofuran / 1 h / -40 °C 2: 88 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: hydrogen bromide; bromine; acetic acid / dichloromethane / Reflux 2.1: water; acetonitrile / 0.08 h 2.2: Reflux 3.1: sodium hydroxide / 2 h / 0 - 10 °C 4.1: 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-[1,3,5]triazine / N,N-dimethyl-formamide / 4 h / Reflux 5.1: sodium hydroxide / ethanol / 1 h / Cooling View Scheme

1: DBBA; hydrogen bromide; acetic acid / dichloromethane / 25 °C / |Large scale 2: sodium acetate / water; acetonitrile / 3 h / 40 °C / |Large scale 3: sodium hydroxide / water / 1.5 h / 40 °C / |Large scale 4: 2-chloro-4,6-dimethoxy-[1,3,5]triazine; 4-methylmorpholine N-oxide / N,N-dimethyl-formamide / 1.5 h / 25 °C / |Large scale View Scheme

1: DBBA; hydrogen bromide; acetic acid / dichloromethane / 25 °C / |Large scale 2: sodium acetate / water; acetonitrile / 3 h / 40 °C / |Large scale 3: sodium hydroxide / water / 1.5 h / 40 °C / |Large scale View Scheme

1: DBBA; hydrogen bromide; acetic acid / dichloromethane / 25 °C / |Large scale 2: sodium acetate / water; acetonitrile / 3 h / 40 °C / |Large scale 3: sodium hydroxide / water / 1.5 h / 40 °C / |Large scale 4: 2-chloro-4,6-dimethoxy-[1,3,5]triazine; 4-methylmorpholine N-oxide / N,N-dimethyl-formamide / 1.5 h / 25 °C / |Large scale 5: ethanol / 3 h / |Reflux; |Large scale View Scheme