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

Jing He, Lawrence G. Hamann, Huw M. L. Davies () and Rohan E. J. Beckwith ()
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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

Nature Communications, 2015, vol. 6, issue 1, 1-9

Abstract: 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.

Date: 2015
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DOI: 10.1038/ncomms6943

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