1: penta-2,4-diyn-1-ol With n-butyllithium in tetrahydrofuran; hexane T=-80°C; 0.5 h; 2: 1-iodo-n-heptane With N,N,N',N',N'',N''-hexamethylphosphoric triamide in tetrahydrofuran; hexane T=-30 - 20°C;

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine in tetrahydrofuran 0.5 h; Ambient temperature;

pyrrolidine; copper(l) iodide Alkylation;

1.1: 80 percent / K2CO3 / methanol / 1 h / 20 °C 2.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -80 °C 2.2: 62 percent / HMPA / tetrahydrofuran; hexane / -30 - 20 °C View Scheme

1: N-iodosuccinimide; AgNO3 / acetone 2: 89 percent / pyrrolidine; CuI View Scheme

n-butyllithium; diisobutylaluminium hydride 1.) THF, heptane, -80 deg C, 2.) heptane, -80 deg C, 1 h; 0 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;