1: 1.) Ag2O, Drierite / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature, 3 d 2: 80 percent / NaOMe / methanol / 12 h View Scheme

water in dimethylsulfoxide-d6 T=20°C; 4383 h;

1: 1.) Ag2CO3, Drierite, 2.) I2 / 1.) Et2O, RT, 10 min, 2.) Et2O, RT, 14 h 2: 97.7 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme

Prunus domestica prune seed meal T=50°C; pH=6; 72 h; aq. phosphate bufferIonic liquidEnzymatic reaction;

water T=37°C; 2 h; incubation with tannase;

1: 93 percent / BBr3 / CH2Cl2 / 0.5 h / -78 °C 2: 95 percent / concd aq. HCl / 0.5 h / Heating 3: 90 percent / NaBH4 / H2O / 8 h / Ambient temperature 4: 73 percent / 1N aq. NaOH / tetrahydrofuran / 1 h / Ambient temperature 5: 1.) Ag2CO3, Drierite, 2.) I2 / 1.) Et2O, RT, 10 min, 2.) Et2O, RT, 14 h 6: 97.7 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme

1: 95 percent / concd aq. HCl / 0.5 h / Heating 2: 90 percent / NaBH4 / H2O / 8 h / Ambient temperature 3: 73 percent / 1N aq. NaOH / tetrahydrofuran / 1 h / Ambient temperature 4: 1.) Ag2CO3, Drierite, 2.) I2 / 1.) Et2O, RT, 10 min, 2.) Et2O, RT, 14 h 5: 97.7 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme

1: 90 percent / NaBH4 / H2O / 8 h / Ambient temperature 2: 73 percent / 1N aq. NaOH / tetrahydrofuran / 1 h / Ambient temperature 3: 1.) Ag2CO3, Drierite, 2.) I2 / 1.) Et2O, RT, 10 min, 2.) Et2O, RT, 14 h 4: 97.7 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme

1: 1.) Mg / 1.) THF, 20 deg C, 30 min, 2.) THF, from 10 deg C to 25 deg C, 1.5 h 2: 93 percent / BBr3 / CH2Cl2 / 0.5 h / -78 °C 3: 95 percent / concd aq. HCl / 0.5 h / Heating 4: 90 percent / NaBH4 / H2O / 8 h / Ambient temperature 5: 73 percent / 1N aq. NaOH / tetrahydrofuran / 1 h / Ambient temperature 6: 1.) Ag2CO3, Drierite, 2.) I2 / 1.) Et2O, RT, 10 min, 2.) Et2O, RT, 14 h 7: 97.7 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme

hydrogenchloride; water in methanol T=90°C; 3 h;