Biomimetic synthesis of bis-α-substituent pyrrolidine alkaloids based on a proposed biosynthetic pathway

Abstract

A possible biosynthetic pathway of bis-α-substituent pyrrolidine alkaloids was proposed. Based on the proposed biosynthetic pathway, six pyrrolozoxazine alkaloids and one N-alkyl-5-hydroxymethyl-pyrrole-2-carbaldehyde alkaloid were synthesized. In a mixture of acetic acid and triethylamine, condensation of d-fructose and d-amino acids produced pyrrolozoxazine alkaloids. Replacing d-amino acids with tyramine can afford pyrrolezanthine—a N-alkyl-5-hydroxymethyl-pyrrole-2-carbaldehyde alkaloid.