Convergent Synthesis of Deoxypropionates

Authors

  • Peter S. Diez,

    1. Department of Chemistry, The Scripps Research Institute, 130 Scripps Way #3A2, Jupiter, FL 33458 (USA)
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  • Prof. Glenn C. Micalizio

    Corresponding author
    1. Department of Chemistry, The Scripps Research Institute, 130 Scripps Way #3A2, Jupiter, FL 33458 (USA)
    • Department of Chemistry, The Scripps Research Institute, 130 Scripps Way #3A2, Jupiter, FL 33458 (USA)
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  • The authors acknowledge financial support by the National Institutes of Health–NIGMS (GM80266 and GM80266-04S1). The authors thank the Periana laboratory for assistance with all hydrogenation reactions, and Prof. Kevin Burgess for helpful discussions in the pursuit of a catalyst-controlled stereoselective hydrogenation.

Abstract

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Metallacycle-mediated allylic alcohol–alkyne reductive cross-coupling is described as a convergent solution to the synthesis of deoxypropionates. This approach offers superior step-economy in comparison to available strategies based on multistep iterative chain elongation. The technique is demonstrated in a concise synthesis of the C1–C11 subunit of borrelidin, and a total synthesis of (−)-vittatalactone.

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