A synthetic and in silico study on the highly regioselective Diels–Alder reaction of the polyenic antifungal antibiotics natamycin and flavofungin

Abstract

The tetraenic macrolide antibiotic natamycin and the pentaenic macrolide flavofungin gave monoadducts on Diels–Alder reaction with 4-phenyl-1,2,4-triazoline-3,5-dione. The regioselectivity of the reaction as well as the conformation of the products was studied using theoretical calculations.