1.1: n-butyllithium / tetrahydrofuran / -78 - 20 °C 2.1: manganese(IV) oxide / dichloromethane / 0 - 20 °C 2.2: 50 °C 3.1: iodine / methanol / 5 h / 20 °C 4.1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / N,N-dimethyl-formamide / 100 °C 5.1: Grubb's 2nd generation catalyst / dichloromethane / Reflux 6.1: palladium 10 on activated carbon; oxygen / toluene / Molecular sieve; Reflux View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -40 °C 1.2: tetrahydrofuran; hexane / 2.5 h / -40 - 20 °C 2.1: 3.59 g / p-toluenesulfonic acid monohydrate / methanol / 12 h / 20 °C 3.1: 57 percent / [Rh(cod)2]BF4; (R,R)-(OMe)2-(PPh2)2-1,1';3',3'';1'',1'''-(naphthyl)4; aq. KOH / tetrahydrofuran / 24 h / 60 °C 4.1: 43 percent / LiAlH4 / diethyl ether / 0.5 h / 0 °C 5.1: 76 percent / TBAF / tetrahydrofuran / 3 h / 20 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran / -78 - 20 °C 2.1: manganese(IV) oxide / dichloromethane / 0 - 20 °C 2.2: 50 °C 3.1: iodine / methanol / 5 h / 20 °C 4.1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / N,N-dimethyl-formamide / 100 °C 5.1: Grubb's 2nd generation catalyst / dichloromethane / Reflux View Scheme