NH4PF6; [(η5-C5H5)Ru(PPh3)2Cl] T=100°C; 1 h;

1: 86 percent / BuLi / tetrahydrofuran / 18 h / Heating 2: 1.) dicyclohexylborane, 2.) AcOH / 1.) THF, r.t., 2 h, 2.) THF, r.t., 1 h 3: Br2 / CH2Cl2 / 0.17 h / -78 °C 4: NaOMe / methanol / 1.) 0 deg C, 1 h, 2.) r.t., 2 h 6: 43 percent / n-BuLi / tetrahydrofuran; hexane / 24 h / Ambient temperature 7: 51 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h 8: LiAlH4 / diethyl ether / 3 h / 0 °C 9: imidazole / dimethylformamide / 1 h / Ambient temperature 10: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h 11: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature 12: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature 13: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature 14: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C 15: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature 16: benzenesulfonyl chloride, pyridine / 15 h / 0 °C 17: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h 18: DCC, DMAP / CH2Cl2; dimethylformamide / 1 h / Ambient temperature View Scheme

1: 1-tridecyne With n-butyllithium in tetrahydrofuran T=-70°C; 2: carbon dioxide in tetrahydrofuran 3: With ammonium chloride in tetrahydrofuran; water

1: n-BuLi / hexane; tetrahydrofuran / 1 h / 0 °C 2: aq. LiOH / methanol / 12 h / Ambient temperature View Scheme

n-butyllithium in tetrahydrofuran; hexane T=20°C; 1 h;

1: 1.) hexamethylphosphoramide (HMPA), nBuLi, 2.) HMPA / 1.) hexane, 30 min, 2.) RT, overnight 2: Li, 1,3-diaminopropane, potassium tert-butoxide / 2 h 3: 86 percent / pyridinium dichromate (PDC) / dimethylformamide / 9 h View Scheme

n-butyllithium 1.) HMPA;

(i) LiNH2, liq. NH3, THF, (ii) /BRN= 1745664/, THF; Multistep reaction;