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Synthesis of acyloin natural products by Mukaiyama hydration.
Ricca, Michael; Zhang, Wei; Li, Jiaqi; Fellowes, Thomas; White, Jonathan M; Donnelly, Paul S; Rizzacasa, Mark A.
Affiliation
  • Ricca M; School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria 3010, Australia. masr@unimelb.edu.au.
  • Zhang W; School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria 3010, Australia. masr@unimelb.edu.au.
  • Li J; School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria 3010, Australia. masr@unimelb.edu.au.
  • Fellowes T; School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria 3010, Australia. masr@unimelb.edu.au.
  • White JM; School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria 3010, Australia. masr@unimelb.edu.au.
  • Donnelly PS; School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria 3010, Australia. masr@unimelb.edu.au.
  • Rizzacasa MA; School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria 3010, Australia. masr@unimelb.edu.au.
Org Biomol Chem ; 20(19): 4038-4047, 2022 05 18.
Article in En | MEDLINE | ID: mdl-35506986
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.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Biological Products Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2022 Type: Article Affiliation country: Australia
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Biological Products Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2022 Type: Article Affiliation country: Australia