Molecular basis of elansolid biosynthesis: Evidence for an unprecedented quinone methide initiated intramolecular diels-alder cycloaddition/ macrolactonization

Article abstract of DOI:10.1002/anie.201006880

Total control: The key steps in the biosynthesis of elansolide A1, a new and structurally unique polyketide metabolite from the gliding bacterium Chitinophaga sancti, have been elucidated from feeding experiments, by analysis of the biosynthetic gene cluster, and through the synthesis of model substrates. These steps include an unprecedented dehydration reaction, an intramolecular Diels-Alder cycloaddition (IMDA), and an unusual macrolactonization.