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  • Title: Enantioselective reductive coupling of alkynes and alpha-keto aldehydes via rhodium-catalyzed hydrogenation: an approach to bryostatin substructures.
    Author: Cho CW, Krische MJ.
    Journal: Org Lett; 2006 Mar 02; 8(5):891-4. PubMed ID: 16494467.
    Abstract:
    Hydrogen-mediated reductive coupling of glyoxal 2 and 1,3-enyne 3 provides alpha-hydroxy ketone 4 in 70% yield and 91% enantiomeric excess. Notably, the benzylic ether and diene side chain of 4 remain intact under the conditions of hydrogen-mediated coupling. In four steps, alpha-hydroxy ketone 4 is converted to pyrans 8 and 9, which embody key structural features of the bryostatin recognition domain.
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