Biomimetic synthesis of brevicolline from tryptophan, acetaldehyde, and N-methyl-Δ1-pyrrolinium acetate
Abstract
1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, produced in situ from tryptophan and acetaldehyde, was oxidatively decarboxylated with sodium hypochlorite affording a dihydro-β-carboline which on condensation with N-methyl-Δ1-pyrrolinium acetate and subsequent aerial oxidation afforded brevicolline.