1: 1) n-BuLi, 2) s-BuLi / 1) THF, -78 deg C, 1 h, 2) 1 h 2: 1) TMSCl, LiBH4, 2) K2CO3 / 1) CH3CN, -10 to 25 deg C, 4 h, 2) acetone, reflux, 2.5 h 3: 1) SeO2, t-BuOOH, 2) NaBH4 / 1) CH2Cl2, 0 deg C, 8 h, 2) MeOH 4: 1) MsCl, Et3N, 2) LiBr / 1) CH2Cl2, -40 to -20 deg C, 1 h, 2) THF, -20 to 25 deg C, 2 h 5: 85 percent / NaH, n-BuLi / tetrahydrofuran / 1 h / 0 °C 6: 55 percent / Mn(OAc)3*2H2O / acetic acid / 1 h / 70 °C View Scheme

1: 1.) tetramethylethylenediamine (TMEDA), n-butyllithium, 3.) concd HCl 2: 5.3 g / toluene / 24 h / Heating 3: 95percent hydrazine hydrate / ethanol / 0.5 h / Heating 4: 0.5 h / 320 °C 5: p-TSA / methanol / 1 h / 110 °C 6: 2 N HCl (aqueous) / methanol / 0.5 h / Heating View Scheme

1.1: N,N,N',N'-tetramethylethylenediamine; n-BuLi / hexane; diethyl ether / 0 °C 1.2: hexane; diethyl ether 2.1: 460 mg / aq. HCl / tetrahydrofuran / 20 °C View Scheme