New metal-mediated cyclisation methods for the generation of heteroatom functionalised polycyclic systems.

Lead Research Organisation: University of Strathclyde
Department Name: Pure and Applied Chemistry

Abstract

The preparation of suitably functionalised polycyclic systems in a direct and efficient manner is a widely explored area within organic synthesis. Most commonly, metal-mediated transformations are being applied to access increasingly more diverse and desirable structural frameworks, and through a reduced number of steps. In relation to this, the Pauson-Khand reaction (PKR) represents a powerful and effective technique, which has found increasing use as the key transformation in the synthesis of natural products and other cyclic compounds. Having stated this, within the emerging methods, the substrate scope remains somewhat limited, with bicyclic motifs derived from standard alkyne and (most often strained) alkene components being most readily prepared. More specifically and with regards to the alkene component of this cycloaddition reaction, there are very few examples of more functionalised partners, such as those containing additional heteroatoms, which provide more diverse cyclopentenone products with potentially pharmaceutically useful functionality.
This collaborative programme between Kerr and GSK partners will explore novel heteroatom containing substrates for the Pauson-Khand cyclisation reaction to construct an array of decorated cyclopentenone products. Such methods will deliver a preparatively flexible and powerful range of techniques to allow access to a variety of pharmaceutically-desired organic compounds and natural products, all whilst increasing the overall capacity of the reaction.
As part of the overall programme of work, computationally-driven methods will be used to deliver enhanced understanding of reaction mechanism and catalyst design, as well as the expansion of emerging reaction scope.
The main EPSRC research areas addressed are Catalysis, Chemical Reaction Dynamics and Mechanism, and Synthetic Organic Chemistry.

Publications

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Studentship Projects

Project Reference Relationship Related To Start End Student Name
EP/V519777/1 01/10/2020 30/09/2025
2440505 Studentship EP/V519777/1 01/10/2020 30/09/2024 Michael Coombes