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Rhodium(III)-Catalyzed Intramolecular Annulation through C[BOND]H Activation: Total Synthesis of (±)-Antofine, (±)-Septicine, (±)-Tylophorine, and Rosettacin

Authors

  • Dr. Xianxiu Xu,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
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    • These authors contributed equally to this work.

  • Yu Liu,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
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    • These authors contributed equally to this work.

  • Prof. Cheol-Min Park

    Corresponding author
    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
    • Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
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  • We gratefully acknowledge the Nanyang Technological University for the funding of this research. We thank Dr. Rakesh Ganguly for X-ray crystallographic analysis.

Abstract

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Annulation: The efficient synthesis of 3-hydroxyalkyl isoquinolones and 6-hydroxyalkyl 2-pyridones is enabled through the intramolecular annulation of alkyne-tethered hydroxamic esters (see scheme, Cp*=pentamethylcyclopentadienyl). The reaction features high regioselectivity, broad substrate scope, and excellent functional-group tolerance, proceeds under mild reaction conditions with low catalyst loading, and obviates the need for an external oxidant.

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