hydrogen; palladium on activated charcoal in ethanol Hydrogenolysis; P=5171.48 - 6205.78 Torr; 2 h;

1: 97 percent / AcOD; salicylaldehyde / 1 h / 100 °C 2: Na2CO3; NaHCO3 / H2O; dioxane / 12 h / 50 °C / pH 9.5 3: 89 percent / H2 / Pd/C / ethanol / 2 h / 5171.48 - 6205.78 Torr View Scheme

1: Na2CO3; NaHCO3 / H2O; dioxane / 12 h / 50 °C / pH 9.5 2: 89 percent / H2 / Pd/C / ethanol / 2 h / 5171.48 - 6205.78 Torr View Scheme

Zn(ClO4)2; (S)-15-aminomethyl-14-hydroxy-5,5-dimethyl-2,8-dithialt;9gt;(2,5)pyridinophane in methanol-d1 96 h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

dipotassium hydrogenphosphate; potassium dihydrogenphosphate; pyridoxal 5'-phosphate; water-d2 T=30°C; 24 h; Escherichia coli B/1t/-A cells (containing tryptophanase); Yield given;

hydrogenchloride; Dowex 50-WX8; acetic acid; trifluoroacetic acid 1.) CH2Cl2, 30 min, 0 deg C; 12 h, room temperature; 2.) 100-105 deg C, toluene, water, 58 h; Yield given. Multistep reaction;

1: 1.) lithium diisopropylamine, n-BuLi; 2.) D2O / 1.) THF, hexane, -78 deg C, 70 min; 2.) THF, hexane, -78 deg C warming to room temperature, 3 h 2: 1.) trifluoroacetic acid; 2.) 0.75M HCl, Dowex 50-WX8, acetic acid / 1.) CH2Cl2, 30 min, 0 deg C; 12 h, room temperature; 2.) 100-105 deg C, toluene, water, 58 h View Scheme