Novel rearrangement of the ionophore antibiotic X-14547A (indanomycin) and related derivatives induced by lithium tetrafluoroborate

Abstract

Stereospecific rearrangement of the ionophore antibiotic X-14547A (indanomycin) and related derivatives, occurs readily at 70 °C in acetonitrile solution containing lithium tetrafluoroborate. The product of the reaction is a novel tetracyclic compound derived by ring cleavage of the tetrahydropyranyl ring, with concomitant double-bond migration and intramolecular cyclisation involving a pyrrole group.