NMR, Computation and Total Synthesis; Uncovering the Stereochemistry of 1,5-polyol-containing Macrolides

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Amantelide A is one of a group of polyhydroxylated macrolide natural products furnished with a repeated sequence of 1,5-related stereogenic centers. Such 1,5-polyol motifs represent a significant challenge for their synthesis, NMR and computational analyses, as the remote position of the stereocenters can complicate these elements. This project aims to develop a general procedure for assigning the stereochemical configuration of highly furnished polyhydroxylated molecules with distal stereocenters. More broadly we aim to 'fingerprint' such molecules in such a way as to derive the configurational relationships between contiguous stereocenters without the explicit need to synthesise their parent compounds. A synergistic approach combining the efficient and stereoselective synthetic methodologies developed within the Aggarwal group with the advanced NMR and computational analyses of the Butts group could afford a reliable methodology for uncovering the stereochemistry otherwise challenging macrocyclic compounds.