1.1: 10 palladium on activated charcoal; hydrogen / ethyl acetate / 20 °C 2.1: water; sodium hydroxide / methanol / Reflux; Inert atmosphere 3.1: bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; triphenylphosphine / 1,4-dioxane / Reflux 3.2: 20 °C View Scheme

1.1: water; sodium hydroxide / methanol / Reflux; Inert atmosphere 2.1: bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; triphenylphosphine / 1,4-dioxane / Reflux 2.2: 20 °C View Scheme

1.1: potassium tert-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: 10 palladium on activated charcoal; hydrogen / ethyl acetate / 20 °C 3.1: water; sodium hydroxide / methanol / Reflux; Inert atmosphere 4.1: bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; triphenylphosphine / 1,4-dioxane / Reflux 4.2: 20 °C View Scheme

potassium tert-butylate in ammonia 2 h; Photolysis;

1: p-TsOH / toluene / 15 h / Heating 2: 4.59 g / LDA*THF / tetrahydrofuran; cyclohexane / 5 h / Heating View Scheme

hydrogenchloride T=150°C;

PPA

boron trifluoride diethyl etherate; acetic acid; lithium diisopropyl amide 1.) THF/hexane/HMPA, -78 deg C, 3 h; 2.) 105 deg C, 1.25 h; 3.) reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;