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Practical and Catalytic Stereoselective Synthesis of Versatile Tetrasubstituted Alkenes

Project description

Innovative stereoselective synthesis of alkene-containing compounds

Alkene-containing molecules and their derivatives are key ingredients in polymer science and materials research and are in high demand in medicine, food, and energy production. Most applications require alkenes and the derivatives to be present in isomerically pure form. Funded by the Marie Skłodowska Curie Actions programme, the TETRASYN project aims to develop a stereoselective synthesis of various tetrasubstituted alkenes from commercially available diboron compounds, using Cu based catalysts, nitriles and allenes. The resulting tetrasubstituted alkene products will contain modifiable functional groups and provide a source for a spectrum of derivatives. The objective is to prove the applicability of the approach via stereoselective synthesis of neocurcumenol, a natural anti inflammation medicine, and acolbifene, an experimental breast cancer treatment drug.

Objective

Alkene-containing molecules and their derivatives play a major role in medicine, food and energy production, as well as materials research and polymer science. In most applications, particularly in medicine, alkenes are needed in isomerically pure form. While strategies for stereoselective preparation of olefins have been the subject of substantial interest, methods relating to synthesis of tetrasubstituted alkenes are uncommon, especially those that are catalytic. What is more, the small number of available protocols are often not highly selective or broadly applicable. The goal of the proposed studies is to introduce a practical, scalable, modular and highly stereoselective synthesis of a large assortment tetrasubstituted alkenes from readily available Cu-based catalysts, nitriles, allenes, and a commercially available diboron compound. The tetrasubstituted alkene products will contain readily modifiable functional groups, such as a ketone, an ester, and a boronate moiety, thus offering direct access to a larger collection of otherwise difficult-to-prepare and much sought-after derivatives. The applicability of the approach will be highlighted by a concise and practical gram-scale stereoselective synthesis of two important bioactive compounds. The first will be neocurcumenol, a natural product with anti-inflammatory properties, and the second will be acolbifene, currently in third phase clinical trials for treatment of breast cancer. Equally important, the versatility of the catalytic strategy will allow for facile preparation of host of related analogues – entities that might display superior pharmacological properties and cannot be synthesized easily by the available methods.

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MSCA-IF - Marie Skłodowska-Curie Individual Fellowships (IF)

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Call for proposal

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(opens in new window) H2020-MSCA-IF-2020

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Coordinator

UNIVERSITE DE STRASBOURG
Net EU contribution

Net EU financial contribution. The sum of money that the participant receives, deducted by the EU contribution to its linked third party. It considers the distribution of the EU financial contribution between direct beneficiaries of the project and other types of participants, like third-party participants.

€ 196 707,84
Address
RUE BLAISE PASCAL 4
67081 STRASBOURG
France

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Activity type
Higher or Secondary Education Establishments
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Total cost

The total costs incurred by this organisation to participate in the project, including direct and indirect costs. This amount is a subset of the overall project budget.

€ 196 707,84
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