1: O-MOM-sesamol With n-butyllithium; N,N,N',N,-tetramethylethylenediamine in hexane T=0°C; 2: methyl iodide in diethyl ether; hexane T=-78 - 20°C; Further stages.;

1.1: 4.7 g / ethyldiisopropylamine / CH2Cl2 / 0 - 20 °C 2.1: n-butyl lithium / tetrahydrofuran; hexane / 0.17 h / -78 °C 2.2: 90 percent / tetramethylethylenediamine / tetrahydrofuran; hexane / 12 h / -78 - 20 °C View Scheme

1.1: potassium hydroxide / methanol; H2O 2.1: 4.7 g / ethyldiisopropylamine / CH2Cl2 / 0 - 20 °C 3.1: n-butyl lithium / tetrahydrofuran; hexane / 0.17 h / -78 °C 3.2: 90 percent / tetramethylethylenediamine / tetrahydrofuran; hexane / 12 h / -78 - 20 °C View Scheme

1.1: m-chloroperoxybenzoic acid / CH2Cl2 / 18 h / Heating 2.1: potassium hydroxide / methanol; H2O 3.1: 4.7 g / ethyldiisopropylamine / CH2Cl2 / 0 - 20 °C 4.1: n-butyl lithium / tetrahydrofuran; hexane / 0.17 h / -78 °C 4.2: 90 percent / tetramethylethylenediamine / tetrahydrofuran; hexane / 12 h / -78 - 20 °C View Scheme

1: 77 percent / conc. aq. HCl / ethanol / 3 h / Heating 2: 73 percent / acetic acid / 0.5 h / Heating View Scheme

1: 1.) BuLi / 1.) THF, -30 deg C, 13 h 2: CH3SO3H / CH2Cl2 / 0 °C 3: 1.) NaH / 1.) DMF, 0 deg C, 5 min, 2.) DMF, 23 deg C, 40 min 4: 99 percent / piperidine, acetic acid / benzene / 18 h / 23 °C 5: 94 percent / Et3N, HCOOH, Pd(PPh3)4 / 4 h / 23 °C 6: (PhO)2P(O)N3, Et3N, 4 Angstroem molecular sieves / toluene / 2 h / 70 °C 7: 1 h / 23 °C 8: 97 percent / H2, Rh<(COD)-(R,R)-DIPAMP>(+)*BF4(-) / 16 h / 23 °C / 2280 Torr 9: BF3*Et2O, H2O / CH2Cl2 / 0.17 h / 0 °C 10: BF3*Et2O, 4 Angstroem molecular sieves / CH2Cl2 / 18 h / 23 °C 11: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 6 h / 23 °C / 760 Torr 12: 61 percent / HOAc / 18 h / 23 °C 13: 87 percent / Cs2CO3 / dimethylformamide / 1 h / 23 °C 14: diisobutylaluminum hydride / toluene / 5 h / -78 °C 15: KF*2H2O / methanol / 0.33 h / 23 °C 16: CH3SO3H, 3 Angstroem molecular sieves / CH2Cl2 / 5 h / 23 °C 17: 72 percent / Et3N, DMAP / CH2Cl2 / 6 h / 23 °C 18: 89 percent / DMAP / CH2Cl2 / 13 h / 23 °C 19: 92 percent / i-Pr2NEt / CH2Cl2 / 0.33 h / 23 °C 20: 1.) Bu3SnH, PdCl2(PPh3)2, HOAc, 2.) NaBH3CN, HOAc / 1.) CH2Cl2, 23 deg C, 15 min, 2.) CH3CN, 23 deg C, 30 min 21: 83 percent / PdCl2(PPh3)2, LiCl / dimethylformamide / 2 h / 80 °C 22: (PhSeO)2O / CH2Cl2 / 0.25 h / 23 °C 23: Bu4NF / tetrahydrofuran / 0.17 h / 23 °C 24: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / CH2Cl2 / 0.5 h / 23 °C 25: 0.5 h / -40 °C 26: 1.) i-Pr2NEt, 2.) tert-butyl alcohol, N-tert-butyl-N',N',N'',N''-tetramethylguanidine / 1.) 0 deg C, 30 min, 2.) 23 deg C 27: 23 °C 28: 84 percent / PdCl2(PPh3)2, Bu3SnH, HOAc / CH2Cl2 / 0.08 h / 23 °C 29: 70 percent / <N-methylpyridinium-4-carboxaldehyde>iodide, 1,8-diazabicyclo<6.4.0>undec-7-ene, DMF / CH2Cl2 / 0.67 h / 23 °C 30: 82 percent / silica gel / ethanol / 23 °C 31: aq. CF3COOH / tetrahydrofuran / 9 h / 23 °C 32: aq. AgNO3 / acetonitrile / 11 h / 23 °C View Scheme

1: HCl / ethanol / Heating 2: 3.0 g / potassium carbonate / acetone / 5 h / Heating View Scheme