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

Projektinformationen

PHOTOLITH

ID Finanzhilfevereinbarung: 101023251

DOI

10.3030/101023251

Projekt abgeschlossen

EK-Unterschriftsdatum 23 Februar 2021

Startdatum 8 Juni 2021

Enddatum 7 Juni 2023

Finanziert unter

• EXCELLENT SCIENCE - Marie Skłodowska-Curie Actions

Gesamtkosten

€ 212 933,76

EU-Beitrag

€ 212 933,76

Koordiniert durch

UNIVERSITY OF BRISTOL
United Kingdom

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

Berichtszeitraum: 2021-06-08 bis 2023-06-07

Zusammenfassung vom Kontext und den Gesamtzielen des Projekts

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.

Arbeit, die ab Beginn des Projekts bis zum Ende des durch den Bericht erfassten Berichtszeitraums geleistet wurde, und die wichtigsten bis dahin erzielten Ergebnisse

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.

Fortschritte, die über den aktuellen Stand der Technik hinausgehen und voraussichtliche potenzielle Auswirkungen (einschließlich der bis dato erzielten sozioökonomischen Auswirkungen und weiter gefassten gesellschaftlichen Auswirkungen des Projekts)

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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