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

He, Jing and Hamann, Lawrence and Davies, Huw and Beckwith, Rohan (2015) Late-stage C-H functionalization of complex alkaloids & drug molecules via intermolecular rhodium-carbenoid insertion. Nature Communications.

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)-catalyzed intermolecular C-H insertion into complex natural products containing nucleophilic tertiary amines. 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.

Item Type: Article
Keywords: Late-stage C-H functionalization, natural products, alkaloids, C-H activation,
Date Deposited: 28 Apr 2016 23:45
Last Modified: 28 Apr 2016 23:45
URI: https://oak.novartis.com/id/eprint/21312

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