1: With tert.-butyl lithium in tetrahydrofuran; pentamethylene T=-78°C; Substitution; 0.25 h; 2: With boric acid trimethyl ester in tetrahydrofuran; pentamethylene T=-78 - 20°C; Substitution; Further stages.;

1: With n-butyllithium in tetrahydrofuran; hexane; water T=-78 - 40°C; 2.66667 h; Inert atmosphere; 2: With hydrogenchloride in tetrahydrofuran; hexane; water

1.1: 96 percent / 1,3-dibromo-5,5-dimethylhydantoin / tetrahydrofuran / 24 h / 0 °C 2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 2.2: tetrahydrofuran / 24 h / -78 °C 3.1: Acid hydrolysis View Scheme

in tetrahydrofuran react. under N2; THF cooled to -60°C, addn. of borate and Grignard reagent in THF simultaneously (equimolar amts. over whole period of react.), then stirred for 30 min at -60°C, warmed to room temp., stirred for 30 min;; treated with water, extd. with Et2O, organic layers extd. with 1M aq. NaOH, aq. layers acidified with 2M aq. HCl, extd. with CH2Cl2, organic layers dried (MgSO4), filtered, concentrated, recrystd. from ethanol/water;;

in phosphate buffer pH=6.9 - 7.0; Kinetics;

palladium diacetate; potassium carbonate; triphenylphosphine in water; isopropyl alcohol T=90°C; Suzuki coupling; 18 h; Inert atmosphere;

tetrakis(triphenylphosphine) palladium(0); potassium carbonate in tetrahydrofuran; water Suzuki coupling; 72 h; Reflux;

tetrabutylammomium bromide; potassium carbonate; palladium diacetate in water Condensation;

potassium phosphate; palladium diacetate; triphenylphosphine in toluene T=100°C; Suzuki coupling; 16 h; Inert atmosphere;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether 17 h; Heating;