Synthesis of new macrocycles. Part 6. Pyridine-retronecate, a new synthetic alkaloid

Abstract

Reaction of 2,6-bis(bromomethyl)pyridine with the naturally-occurring C₁₀ necic acid, retronecic acid, results in the formation of a new semi-synthetic cyclic diester alkaloid, pyridine-retronecate. This product is an analogue of a pyrrolizidine alkaloid and retains those characteristics normally held responsible for the toxicity of this class of alkaloids. Biological tests carried out on mice injected with retrorsine and with the synthetic analogue suggest that the cytotoxic effects are similar.