NEDRATS · New Enantioselective Desymmetrization Reactions in Alkaloid Total Synthesis
Horizon 2020 — Marie Skłodowska-Curie Actions
- Duration
- 2015-07-06 → 2017-07-05
- EU contribution
- €195,455
- Participants
- 1
- Scheme
- MSCA-IF
Lines connect the coordinator with its partners.
Results in brief
New Enantioselective Desymmetrization Reactions in Alkaloid Total Synthesis
The aim of this project was to develop a new, synthetically powerful and broadly applicable asymmetric methodology for the synthesis of alkaloids and related natural products in a concise series of transformations. The enantioselective construction of the key core will be achieved by development of a novel and highly selective desymmetrisation reaction of unsaturated alkene- or allylic alcohol-linked cyclohexanones by means of a dual cooperative catalytic system comprised of a chiral organocatalyst and a metal catalyst. Alkenes and allylic alcohols would be suitable for this transformation because both are susceptible of metal activation. The amine organocatalyst would be responsible for activating the ketone functionality, and the generated nucleophilic enamine intermediate will then be ready to attack the pendant transition metal-activated alkene/allylic alcohol group.
Data: CORDIS, © European Union
Project objective
This project will develop a new, highly enantioselective, state-of-the-art synthetic route to the daphniyunnine family of alkaloids based on a novel dual organo / metal catalysed desymmetrization reaction of alkene-linked cyclohexanones as a key step, which will allow the rapid and efficient construction of the AB rings ready for subsequent advancement to the majority of the family members. Evaluation of the anti-cancer biological activity of the different target molecules and late stage intermediates will be carried out. This Fellowship project combines total synthesis, new asymmetric methodology development and biological evaluation. It has been designed to augment and complement the research and transferable skills sets of the Marie Curie fellow, Dr Sonawane, and will greatly enhance his career prospects accordingly. Through the training and the research results arising, the Fellowship will be beneficial to the fellow, the host institution and European science.
Original text from CORDIS.
Participants
- THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD · OxfordCoordinatorUnited Kingdom
Links
Data: CORDIS, © European Union