Glyoxylic acid, with tryptamine

Tryptamine, with glyoxylic acid to give 1,2,3,4-tetrahydro-B-carboline, 51, 136... 

Dissolve 4 g glyoxylic acid monohydrate in 220 ml water and add with stirring to a solution of 10 g 4,5, or 6 methoxy-tryptamine-HCl in 80 ml water. Adjust pH to 4 with 10% KOH and stir five hours at room temperature. Filter and wash with water to get about 4.5 g precipitate. Melt to decarboxylate or to 4 g precipitate add 30 ml concentrated HCI and 100 ml water and heat at 65° one hour. Add water to dissolve the solid and add excess 10% KOH. Filter to get the title compound or analog. 

Woodward s strychnine synthesis commences with a Fischer indole synthesis using phenylhydrazine (24) and acetoveratrone (25) as starting materials (see Scheme 2). In the presence of polyphosphor-ic acid, intermediates 24 and 25 combine to afford 2-veratrylindole (23) through the reaction processes illustrated in Scheme 2. With its a position suitably masked, 2-veratrylindole (23) reacts smoothly at the ft position with the Schiff base derived from the action of dimethylamine on formaldehyde to give intermediate 22 in 92% yield. TV-Methylation of the dimethylamino substituent in 22 with methyl iodide, followed by exposure of the resultant quaternary ammonium iodide to sodium cyanide in DMF, provides nitrile 26 in an overall yield of 97%. Condensation of 2-veratryl-tryptamine (20), the product of a lithium aluminum hydride reduction of nitrile 26, with ethyl glyoxylate (21) furnishes Schiff base 19 in a yield of 92%. 

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