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.
S. J. F. Macdonald, T. C. McKenzie and W. D. Hassen, J. Chem. Soc., Chem. Commun., 1987, 1528 DOI: 10.1039/C39870001528
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