1: 91 percent / NaBH4 / ethanol / 3.5 h / 0 - 23 °C 2: 93 percent / tetrahydrofuran; diethyl ether / 3.5 h / 23 °C 3: (-)-sparteine; O2; Cs2CO3 / Pd(nbd)Cl2 / toluene; 2-methyl-propan-2-ol / 4.5 h / 80 °C / 760.05 Torr 4: 90 percent / P(o-tolyl)3; Et3N / Pd(OAc)2 / dimethylformamide / 3 h / 100 °C View Scheme

palladium diacetate; triethylamine; tris-(o-tolyl)phosphine in toluene T=100°C; 1 h; other reagent: triphenylphosphine;

1.1: B-chloro-diisopinocampheylborane / dichloromethane; n-heptane / 8 h / 25 °C 2.1: toluene; tetrahydrofuran / 4 h / 0 - 5 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -20 - -15 °C / |Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -15 °C / |Inert atmosphere 4.2: 5.5 h / -15 - -5 °C / |Inert atmosphere 5.1: palladium diacetate; triphenylphosphine; triethylamine / N,N-dimethyl-formamide / 110 °C 6.1: caustic lye / 12 h / 120 °C View Scheme

1.1: B-chloro-diisopinocampheylborane / dichloromethane; n-heptane / 8 h / 25 °C 2.1: toluene; tetrahydrofuran / 4 h / 0 - 5 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -20 - -15 °C / |Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -15 °C / |Inert atmosphere 4.2: 5.5 h / -15 - -5 °C / |Inert atmosphere 5.1: palladium diacetate; triphenylphosphine; triethylamine / N,N-dimethyl-formamide / 110 °C 6.1: caustic lye / 12 h / 120 °C 7.1: sodium hydroxide / methanol / 1 h / 25 °C View Scheme