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Reagents and conditions: (a) Na, naphthalene, DME, −78 °C, 30 min, 75%; (b) 4N HCl in dioxane, rt, 1 h, 85%; (c) butyraldehyde, NaBH(OAc)3, ClCH2CH2Cl, rt, 16 h, 75%; (d) nonyl aldehyde, NaBH(OAc)3, ClCH2CH2Cl, rt, 16 h, 76%; (e) PdCl2, MeOH, H2, rt, 16 h, 76% for 1, 78% for 2; (f) Li, liquid NH3, THF, −78 °C, 1 h, 59% for 3, 66% for 4.
