1: ω-Hydroxyundecyl triphenylphosphonium bromide With n-butyllithium in tetrahydrofuran; hexane T=-15°C; 2 h; 2: propionaldehyde in tetrahydrofuran; hexane T=-15 - 20°C; 3: acetic anhydride With pyridine T=20°C; 15 h; Further stages. Title compound not separated from byproducts.;

1: 28 percent / DMSO, NaH / tetrahydrofuran / 0.5 h 2: pyridine View Scheme

1: n-BuLi / tetrahydrofuran / 0.5 h 2: 5.4 g / tetrahydrofuran / 3 h / 60 °C 3: 86 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 1) n-BuLi / 1) THF, -30 deg C, 2 h, 2) THF, -78 deg C, 2 h, then -78 dec C -> rt, 16 h 2: 95 percent / tetrahydrofuran / 4 h / Heating 3: 37 percent / LDA / tetrahydrofuran; hexane / 5 h / 0 deg C -> 25 deg C 4: 75 percent / H2 / Pt / ethyl acetate / 48 h / 760 Torr 5: 96 percent / Zn(BH4)2 / diethyl ether / 1) 0 deg C, 3 h, 2) rt, 24 h View Scheme

1: 63 percent / DMSO, NaH / tetrahydrofuran / 0.5 h 2: pyridine View Scheme