Progress towards the total synthesis of the enediyne anticancer antibiotics

Abstract

Progress towards the synthesis of two of the enediyne antibiotics, calicheamicin γ11and dynemicin A, is outlined. The enantioselective total synthesis of the oligosaccharide and aglycone portions of calicheamicin γ11have been achieved, as has a synthesis of a functioning model of dynemicin A. A key reaction in the oligosaccharide synthesis involved a [3,3]-sigmatropic rearrangement of an allylic thionoimidazolide, whilst the aglycone synthesis relied upon an intramolecular alkenyl nitrile oxide dipolar cycloaddition reaction to lead directly to the introduction of the full functionality of the molecule. © 1993 IUPAC