The syntheses of (±)-juglomycin A and (±)-juglomycin B, racemates of two isomeric naturally occurring naphthoquinonoid antibiotics

Abstract

Syntheses of the diastereoisomeric 5-hydroxy-2-(4′-hydroxy-γ-butyrolacton-5′-yl)-1,4-naphthoquinones (1) and (2) and their 5-deoxy-analogues (3) and (4) are described. The stereochemistries of the latter, being defined through unambiguous synthesis, permit the assignment of the configurations of (1) and (2)(which were obtained from a single precursor) and also those of the natural products, juglomycins A and B.