Abstract
Chromones represent a privileged scaffold in medicinal chemistry and are an omnipresent structural motif in natural products. Chemically encoded non-natural peptidomimetics feature improved stability towards enzymatic degradation, cell permeability and binding affinity, translating into a considerable impact on pharmaceutical industry. Herein, a strategy for the sustainable assembly of chromones via electro-formyl C–H activation is presented. The rational design of the rhodaelectro-catalysis is guided by detailed mechanistic insights and provides versatile access to tyrosine-based fluorogenic peptidomimetics.
Highlights
Chromones represent a privileged scaffold in medicinal chemistry and are an omnipresent structural motif in natural products
C–H activation has surfaced as a transformative strategy for molecular synthesis, with remarkable applications to materials science and late-stage diversification[1,2,3,4,5,6]
Functionalizations of hydroxybenzaldehydes have proven to be a enabling approach for the assembly of oxygen-containing heterocycles[9,10,11], such as β-hydroxyketones, aurones, coumarines, and chromones[12,13,14,15,16]. This approach was largely limited by the need for stoichiometric amounts of chemical oxidants, compromising the inherent sustainable nature of the formyl C–H activation strategy
Summary
Chromones represent a privileged scaffold in medicinal chemistry and are an omnipresent structural motif in natural products. We present an electro-formyl C–H activation via rhodaelectro catalysis for the assembly of substituted chromones to provide sustainable access to amino acid Results and discussion To put our hypothesis into practice, we designed intermediates that feature lower oxidation potentials than the sensitive aldehyde substrates themselves (Fig. 1b).
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
