pyridine; lithium chloride in dimethyl sulfoxide T=185°C; 5 h;

copper diacetate in tetrahydrofuran; water 0.666667 h;

1: 1) n-BuLi, triphenylmethane / 1) ether, HMPA, hexane, 0 deg C, 2) ether, 0 deg C, 15 min 2: diethyl ether; hexane; hexamethylphosphoric acid triamide / 3 h / Ambient temperature 3: 1) n-BuLi / 1) THF, HMPA, hexane, -78 deg C, 45 min, 2) THF, -78 deg C to room temperature, overnight 4: 52 percent / Cu(OAc)2*H2O / tetrahydrofuran; H2O / 0.67 h View Scheme

1: 85 percent / p-TsOH / 4 h / Heating 2: 83 percent / DIBAL-H / hexane; benzene / 4 h 3: 92 percent / BuLi, Ph3CH, p-TsCl, LiCl / hexamethylphosphoric acid triamide; hexane; diethyl ether / Ambient temperature 4: 1.) EtMgBr; 2.) 5percent CH3COOH / 1.) THF, 24 h, r.t.; 2.) 0 deg C, THF/H2O View Scheme

1: pyridine, CrO3 / CH2Cl2 2: 5percent AcOH 3: DIBAL-H 4: 92 percent / BuLi, Ph3CH, p-TsCl, LiCl / hexamethylphosphoric acid triamide; hexane; diethyl ether / Ambient temperature 5: 1.) EtMgBr; 2.) 5percent CH3COOH / 1.) THF, 24 h, r.t.; 2.) 0 deg C, THF/H2O View Scheme

1: 83 percent / DIBAL-H / hexane; benzene / 4 h 2: 92 percent / BuLi, Ph3CH, p-TsCl, LiCl / hexamethylphosphoric acid triamide; hexane; diethyl ether / Ambient temperature 3: 1.) EtMgBr; 2.) 5percent CH3COOH / 1.) THF, 24 h, r.t.; 2.) 0 deg C, THF/H2O View Scheme

1: DIBAL-H 2: 92 percent / BuLi, Ph3CH, p-TsCl, LiCl / hexamethylphosphoric acid triamide; hexane; diethyl ether / Ambient temperature 3: 1.) EtMgBr; 2.) 5percent CH3COOH / 1.) THF, 24 h, r.t.; 2.) 0 deg C, THF/H2O View Scheme

1: 30 percent / Irradiation 4: diisobutylaluminium hydride / ethanol 5: 92 percent / lithium chloride, HMPT / diethyl ether View Scheme

3: diisobutylaluminium hydride / ethanol 4: 92 percent / lithium chloride, HMPT / diethyl ether View Scheme

1: 90 percent / DIBAL-H / benzene; hexane 2: pyridine, CrO3 / CH2Cl2 3: 5percent AcOH 4: DIBAL-H 5: 92 percent / BuLi, Ph3CH, p-TsCl, LiCl / hexamethylphosphoric acid triamide; hexane; diethyl ether / Ambient temperature 6: 1.) EtMgBr; 2.) 5percent CH3COOH / 1.) THF, 24 h, r.t.; 2.) 0 deg C, THF/H2O View Scheme