Synthesis of the aglycones of the ravidomycin family of antibiotics

Abstract

The preparation of the aglycones of the ravidomycin family of antibiotics is described, involving the palladium-catalysed coupling of appropriate stannanes with a common tetracyclic bromide (5), the synthesis of which involved Meerwein coupling of an aniline derivative (13) with 2,5-dichloro-1,4-benzoquinone followed by a directed Diels–Alder reaction.