1: 1) Mg / 2) Li2CuCl4 / 1) THF; 2) THF, 5 h, -10 deg C 2: 80 percent / pTsOH, pyridine / methanol / 6 h / 55 °C View Scheme

1: 1.) 60percent NaH, DMSO, room temperatere, 2.) 60percent NaH, 3.) HCl/AcOH 2: 47.3 percent / aluminum amalgum / tetrahydrofuran; H2O / 3 h / Heating 3: 50 percent / 0.5M NaOH / ethanol; H2O / 5 h / Heating View Scheme

1: 1.) LDA; 2.) HMPA / 1.) hexane, THF, 10 min, 0 deg C, 3 min -20 deg C; 2.) hexane, THF, -20 deg C, 1 h; 3.) hexane, THF, -40 deg C, 1 h 2: 90 percent / NaOH 0.67N / aq. ethanol / 16 h / Ambient temperature 3: 90 percent / diethyl ether View Scheme

1: 1.) LDA; 2.) HMPA / 1.) hexane, THF, 10 min, 0 deg C, 3 min -20 deg C; 2.) hexane, THF, -20 deg C, 1 h; 3.) hexane, THF, -40 deg C, 1 h 2: 90 percent / NaOH 0.67N / aq. ethanol / 16 h / Ambient temperature View Scheme

1: 60 percent / LDA / tetrahydrofuran / 1.) -78 deg C to -40 deg C, 2.) -78 deg C 2: 65 percent / HCO2H, NEt3 / PPh3/Pd(OAc)2 / dioxane / 72 h / Heating 3: 83 percent / NaBH4 / tetrahydrofuran; methanol / 1.) 0 deg C to r.t., 2.) 40 deg C, 2 d 4: 98 percent / 2 h / 405 °C / 0.01 Torr 5: 72 percent / H2 / 10percent Pd/CaCO3 / methanol / 12 h / Ambient temperature 6: PCC, sodium acetate / CH2Cl2 / 19 h View Scheme

1: 1.) LDA; 2.) HMPA / 1.) hexane, THF, 10 min, 0 deg C, 3 min -20 deg C; 2.) hexane, THF, -20 deg C, 1 h; 3.) hexane, THF, -40 deg C, 1 h 2: 90 percent / NaOH 0.67N / aq. ethanol / 16 h / Ambient temperature View Scheme

1: 1.) LDA / 1.) THF, hexane, -10 deg C, 15 min, 2.) THF, hexane, -50 deg C, 6 h 2: NaOH / tetrahydrofuran; H2O / 2 h / Ambient temperature 3: 100 percent / O2, methylene blue / methanol / 3 h / 0 °C / Irradiation 4: NaBH4, NaHCO3 / H2O / 2 h / Ambient temperature 5: p-TsOH / benzene / Heating View Scheme

1: 80 percent / methanol / 72 h / Ambient temperature 3: 1) Na/Hg, 2) pyridine, HOAc / 1) MeOH, EtOAc, -35 deg C, 5 h, 2) 0 deg C, overnight View Scheme

(i) sBuLi, pentane, THF, (ii) /BRN= 1839741/, (iii) (heating); Multistep reaction;

1: 9.4 g / KOH, PEG-600 / diethyl ether / 1 h / Heating 2: 2.7 g / Br2 / methanol / 0.5 h View Scheme