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Late-stage C–H functionalization of complex alkaloids and drug molecules via intermolecular rhodium-carbenoid insertion

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  • Jing He

    (Novartis Institutes for BioMedical Research)

  • Lawrence G. Hamann

    (Novartis Institutes for BioMedical Research)

  • Huw M. L. Davies

    (Emory University)

  • Rohan E. J. Beckwith

    (Novartis Institutes for BioMedical Research)

Abstract

Alkaloids constitute a large family of natural products possessing diverse biological properties. Their unique and complex structures have inspired numerous innovations in synthetic chemistry. In the realm of late-stage C–H functionalization, alkaloids remain a significant challenge due to the presence of the basic amine and a variety of other functional groups. Herein we report the first examples of dirhodium(II)-catalysed intermolecular C–H insertion into complex natural products containing nucleophilic tertiary amines to generate a C–C bond. The application to a diverse range of alkaloids and drug molecules demonstrates remarkable chemoselectivity and predictable regioselectivity. The capacity for late-stage diversification is highlighted in the catalyst-controlled selective functionalizations of the alkaloid brucine. The remarkable selectivity observed, particularly for site-specific C–H insertion at N-methyl functionalities, offers utility in a range of applications where efficient installation of synthetic handles on complex alkaloids is desired.

Suggested Citation

  • Jing He & Lawrence G. Hamann & Huw M. L. Davies & Rohan E. J. Beckwith, 2015. "Late-stage C–H functionalization of complex alkaloids and drug molecules via intermolecular rhodium-carbenoid insertion," Nature Communications, Nature, vol. 6(1), pages 1-9, May.
    • Handle: RePEc:nat:natcom:v:6:y:2015:i:1:d:10.1038_ncomms6943
    DOI: 10.1038/ncomms6943
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    Cited by:

    1. Takafumi Yatabe & Kazuya Yamaguchi, 2022. "Regiospecific α-methylene functionalisation of tertiary amines with alkynes via Au-catalysed concerted one-proton/two-electron transfer to O2," Nature Communications, Nature, vol. 13(1), pages 1-9, December.

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