Project description
Transforming alkenes into valuable building blocks for medicine
Allenes are highly prized chemical building blocks thanks to their unique, twisted shapes that allow them to interact with biological targets in ways that other molecules cannot. They are traditionally synthesised from high-value alkynes. While it would be more cost-effective to build them from alkenes as they are abundant chemical raw materials, current methods require extreme temperatures and destructive reagents to do this. Supported by the Marie Skłodowska-Curie Actions programme, the Allenes From Alkenes project will introduce a mild, catalytic framework that will transform ordinary alkenes into complex allenes. Using this method to modify the anti-cancer natural product epothilone C, the project will alter the shape of its molecular ring, creating entirely new structures to help discover more potent cancer treatments.
Objective
Allenes are important to investigations in method development, drug discovery, and design of functional materials. While allenes are generated from alkynes, a method that makes it possible to convert alkenes, which are more abundant and less costly than alkyne, to allenes would be of considerable value. However, such methods are rare and those available require relatively forcing conditions and are not catalytic, limiting the applicability in complex molecule synthesis. Inspired by an unexpected recent discovery by the host group, we will develop a catalytic cross-coupling/elimination (CCE) method that will allow for efficient conversion of alkenes to 1,3-disubstituted allenes. The requisite substrates will be accessed either from olefins via cross-metathesis or from boronic acids/esters via cross-coupling. Cross-coupling will involve readily accessible alkenyl boronates are organohalides and cross-metathesis will be promoted by a Ru, or Mo catalysts, most originally developed by the host group. Our investigations will be guided by specific mechanistic attributes of CCE, as identified through preliminary DFT studies. The utility of catalytic CCE will be demonstrated in two ways: by efficient synthesis of bioactive allenes and through late-stage conversion of anti-cancer natural product epothilone C to its corresponding allenyl variants. These latter compounds highlight the fact that allenes represent a stable form of a twisted alkene (neither E or Z). We will show that through CCE uniquely shaped macrocyclic analogs can be obtained and utilized in lead discovery. The present investigations set the stage for eventual development of a catalytic enantioselective version of CCE.
Fields of science (EuroSciVoc)
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Project’s keywords as indicated by the project coordinator. Not to be confused with the EuroSciVoc taxonomy (Fields of science)
Programme(s)
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Multi-annual funding programmes that define the EU’s priorities for research and innovation.
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HORIZON.1.2 - Marie Skłodowska-Curie Actions (MSCA)
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Funding scheme (or “Type of Action”) inside a programme with common features. It specifies: the scope of what is funded; the reimbursement rate; specific evaluation criteria to qualify for funding; and the use of simplified forms of costs like lump sums.
HORIZON-TMA-MSCA-PF-EF - HORIZON TMA MSCA Postdoctoral Fellowships - European Fellowships
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(opens in new window) HORIZON-MSCA-2025-PF
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67081 Strasbourg
France
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