1: With sodium acetate; potassium carbonate; lithium chloride; palladium diacetate in N,N-dimethyl-formamide T=70°C; asymmetric Heck arylation; 68 h; 2: With hydrogenchloride in N,N-dimethyl-formamide 0.5 h; Title compound not separated from byproducts;

1.1: 4-toluenesulfonic acid monohydrate / 1 h / 0 - 20 °C 2.1: 3.90 g / HCl / toluene / 16 h / 100 °C 3.1: aq. NaOAc; K2CO3; LiCl / Pd(OAc)2 / dimethylformamide / 68 h / 70 °C 3.2: aq. HCl / dimethylformamide / 0.5 h View Scheme

1.1: 3.90 g / HCl / toluene / 16 h / 100 °C 2.1: aq. NaOAc; K2CO3; LiCl / Pd(OAc)2 / dimethylformamide / 68 h / 70 °C 2.2: aq. HCl / dimethylformamide / 0.5 h View Scheme

1: With Oxonereg;; glucose derived ketone; potassium carbonate in ethylene glycol dimethyl ether; acetate buffer T=-10°C; pH=9.3; 8 h; 2: With diethylaluminium chloride in hexane; toluene T=-78°C; 0.25 h; Title compound not separated from byproducts;

1: 89 percent / 60 °C 2: 1.) nBuLi / 1.) THF, 0 deg C, 7 h, 2.) THF, -100 deg C, 3 h 3: 12N HCl / 0.17 h View Scheme