1: 100 percent / hydrogen / 10percent Pd/C / ethyl acetate / Ambient temperature 2: LiAlH4 / tetrahydrofuran / Ambient temperature 3: pyridine / Ambient temperature 4: LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 5: p-TsOH*H2O / dioxane; H2O / 3 h / Heating View Scheme

1: m-chloroperbenzoic acid 2: 21 percent / n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C 3: HgO, BF3-etherate / tetrahydrofuran; H2O / 0.75 h / Ambient temperature 4: pyridine / diethyl ether / 0.5 h / 0 °C 5: 0.67 h / 100 - 110 °C 6: sodium hydride / tetrahydrofuran; paraffin / 0.17 h / 0 - 25 °C 7: 99 percent / H2, NaHCO3 / 10 percent Pd-C / dioxane / 3 h 8: 1.) LDA / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C to RT 9: 1.) zinc acetate; 2.) 5 percent KOH / 1.) acetic acid, reflux, 1 h; 2.) MeOH, reflux, 0.5 h 10: N,N-diethylcyclohexylamine / dioxane / 2 h / 60 °C 11: LiAlH4 / diethyl ether / 1 h / 0 °C 13: (n-Bu)3SnH / toluene / 3 h / Heating 14: 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 21 percent / n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C 2: HgO, BF3-etherate / tetrahydrofuran; H2O / 0.75 h / Ambient temperature 3: pyridine / diethyl ether / 0.5 h / 0 °C 4: 0.67 h / 100 - 110 °C 5: sodium hydride / tetrahydrofuran; paraffin / 0.17 h / 0 - 25 °C 6: 99 percent / H2, NaHCO3 / 10 percent Pd-C / dioxane / 3 h 7: 1.) LDA / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C to RT 8: 1.) zinc acetate; 2.) 5 percent KOH / 1.) acetic acid, reflux, 1 h; 2.) MeOH, reflux, 0.5 h 9: N,N-diethylcyclohexylamine / dioxane / 2 h / 60 °C 10: LiAlH4 / diethyl ether / 1 h / 0 °C 12: (n-Bu)3SnH / toluene / 3 h / Heating 13: 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: pyridine / diethyl ether / 0.5 h / 0 °C 2: 0.67 h / 100 - 110 °C 3: sodium hydride / tetrahydrofuran; paraffin / 0.17 h / 0 - 25 °C 4: 99 percent / H2, NaHCO3 / 10 percent Pd-C / dioxane / 3 h 5: 1.) LDA / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C to RT 6: 1.) zinc acetate; 2.) 5 percent KOH / 1.) acetic acid, reflux, 1 h; 2.) MeOH, reflux, 0.5 h 7: N,N-diethylcyclohexylamine / dioxane / 2 h / 60 °C 8: LiAlH4 / diethyl ether / 1 h / 0 °C 10: (n-Bu)3SnH / toluene / 3 h / Heating 11: 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: HgO, BF3-etherate / tetrahydrofuran; H2O / 0.75 h / Ambient temperature 2: pyridine / diethyl ether / 0.5 h / 0 °C 3: 0.67 h / 100 - 110 °C 4: sodium hydride / tetrahydrofuran; paraffin / 0.17 h / 0 - 25 °C 5: 99 percent / H2, NaHCO3 / 10 percent Pd-C / dioxane / 3 h 6: 1.) LDA / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C to RT 7: 1.) zinc acetate; 2.) 5 percent KOH / 1.) acetic acid, reflux, 1 h; 2.) MeOH, reflux, 0.5 h 8: N,N-diethylcyclohexylamine / dioxane / 2 h / 60 °C 9: LiAlH4 / diethyl ether / 1 h / 0 °C 11: (n-Bu)3SnH / toluene / 3 h / Heating 12: 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 99 percent / H2, NaHCO3 / 10 percent Pd-C / dioxane / 3 h 2: 1.) LDA / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C to RT 3: 1.) zinc acetate; 2.) 5 percent KOH / 1.) acetic acid, reflux, 1 h; 2.) MeOH, reflux, 0.5 h 4: N,N-diethylcyclohexylamine / dioxane / 2 h / 60 °C 5: LiAlH4 / diethyl ether / 1 h / 0 °C 7: (n-Bu)3SnH / toluene / 3 h / Heating 8: 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 0.67 h / 100 - 110 °C 2: sodium hydride / tetrahydrofuran; paraffin / 0.17 h / 0 - 25 °C 3: 99 percent / H2, NaHCO3 / 10 percent Pd-C / dioxane / 3 h 4: 1.) LDA / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C to RT 5: 1.) zinc acetate; 2.) 5 percent KOH / 1.) acetic acid, reflux, 1 h; 2.) MeOH, reflux, 0.5 h 6: N,N-diethylcyclohexylamine / dioxane / 2 h / 60 °C 7: LiAlH4 / diethyl ether / 1 h / 0 °C 9: (n-Bu)3SnH / toluene / 3 h / Heating 10: 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature View Scheme

diethyl ether; magnesium anschliessendes Behandeln mit Sauerstoff;

Morus alba Methylation;

1.1: pyridine / 6 h / Heating 1.2: H2 / Pd/C / ethanol / 16 h / 20 °C / 2585.74 Torr 2.1: aq. TsOH / dioxane / 3 h / 80 °C View Scheme