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

Informazioni relative al progetto

PHOTOLITH

ID dell’accordo di sovvenzione: 101023251

DOI

10.3030/101023251

Progetto chiuso

Data della firma CE 23 Febbraio 2021

Data di avvio 8 Giugno 2021

Data di completamento 7 Giugno 2023

Finanziato da

• EXCELLENT SCIENCE - Marie Skłodowska-Curie Actions

Costo totale

€ 212 933,76

Contributo UE

€ 212 933,76

Coordinato da

UNIVERSITY OF BRISTOL
United Kingdom

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

Periodo di rendicontazione: 2021-06-08 al 2023-06-07

Sintesi del contesto e degli obiettivi generali del progetto

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.

Lavoro eseguito dall’inizio del progetto fino alla fine del periodo coperto dalla relazione e principali risultati finora ottenuti

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.

Progressi oltre lo stato dell’arte e potenziale impatto previsto (incluso l’impatto socioeconomico e le implicazioni sociali più ampie del progetto fino ad ora)

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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