Journal article
Synthesis of acyloin natural products by Mukaiyama hydration
M Ricca, W Zhang, J Li, T Fellowes, JM White, PS Donnelly, MA Rizzacasa
Organic and Biomolecular Chemistry | ROYAL SOC CHEMISTRY | Published : 2022
DOI: 10.1039/d2ob00651k
Abstract
The acyloin natural products are a family of bioactive compounds isolated from fungi and myxobacteria. The total synthesis of 7 members of the acyloin family was achieved via a HWE reaction followed by Mukaiyama-Isayama hydration, using novel Co(ii) and Co(iii) Schiff base SALPN complexes as catalysts for the key enone hydration step. Furthermore, we have shown that a mild acyloin rearrangement is possible under Mukaiyama hydration conditions, which was crucial in the success of this approach.
Grants
Awarded by Australian Research Council
Funding Acknowledgements
We thank the Australian Research Council Discovery Program (DP200100722) and the University of Melbourne Faculty of Science Research Grant Support Scheme for funding. We thank the Australian Synchrotron for beamtime via the Collaborative Access Program (proposal 13618b).