Chemistry of the neopolyoxins,pyrimidine and imidazoline nucleoside peptide antibiotics

New chitin synthetase inhibitors, neopolyoxins A, B, and C were isolated from the culture filtrate of Streptomyces cacaoi subsp. asoensis. Their absolute structures have been established on the basis of chemical and spectroscopic evidence. They are structural analogs of the polyoxins. As a nucleobase, neopolyoxin C possesses uracil, while neopolyoxins A and B contain the imidazoline moiety. A ring contraction reaction of pyrimidine nucleoside into imidazoline nucleoside played a key role in the structure determination of the nucleoside moiety. A similar transformation was suggested for the biosynthesis of neopolyoxins A and B.