Novel Scaffolds by Mild Photochemical Rearrangement of Reactive Enolate and Organolithium Anions

Informations projet

PHOTOLITH

N° de convention de subvention: 101023251

DOI

10.3030/101023251

Projet clôturé

Date de signature de la CE 23 Février 2021

Date de début 8 Juin 2021

Date de fin 7 Juin 2023

Financé au titre de

• EXCELLENT SCIENCE - Marie Skłodowska-Curie Actions

Coût total

€ 212 933,76

Contribution de l’UE

€ 212 933,76

Coordonné par

UNIVERSITY OF BRISTOL
United Kingdom

Periodic Reporting for period 1 - PHOTOLITH (Novel Scaffolds by Mild Photochemical Rearrangement of Reactive Enolate and Organolithium Anions)

Période du rapport: 2021-06-08 au 2023-06-07

Résumé du contexte et des objectifs généraux du projet

The synthesis of potential new pharmaceutical targets and ultimately drug molecules used to treat disease is limited by the ability of chemists to make novel molecular structures. In this work we show that a simple transformation allows a new family of cyclic molecules to be formed in an efficient manner, opening up new scaffolds for use in drug discovery. The original objective was to use light to achieve this aim, but in the event we found an alternative method that gave a range of target structures.

Travail effectué depuis le début du projet jusqu’à la fin de la période considérée dans le rapport et principaux résultats atteints jusqu’à présent

Early work showed that the original plan to use a photochemical rearrangement to form new molecular scaffolds was insufficiently general for use in this project. We therefore shifted to the use of spiral lithium amides to promote rearrangements. Early work by the fellow led to a publication showing that structures related to new drug targets could readily be formed using this method. The fellow then moved onto the application of the method towards the formation of medium ring amine targets, which were successfully formed. A publication on this work is in preparation.

Progrès au-delà de l’état des connaissances et impact potentiel prévu (y compris l’impact socio-économique et les conséquences sociétales plus larges du projet jusqu’à présent)

Previous related work had only used chiral starting materials, and not enantioselective deprotonation to form compounds related to the target structures. In addition, we discovered a new stereo retentive SN1 reaction, which is undergoing further investigation, and forms an important mechanistic discovery not previously observed.

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