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Asymmetric Diene Transmissive Pericyclic Reactions of Dendralenes

   Department of Chemistry

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  Prof Paul Clarke  Applications accepted all year round  Self-Funded PhD Students Only

About the Project

Polycyclic structures are ubiquitous in the natural product arena and are the core structural units of many natural product-based pharmaceuticals. However, their synthesis is non-trivial due to the complexity of these structures. This is due to the large number of possible arrangements of the ring systems, the incorporation of stereogenic centres, and the dizzying array of possible substitutions and functionalisations on the polycyclic core. Historically, the Diels-Alder reaction has been the workhorse method for the synthesis of polycyclic molecules, but its application can be limited by the availability of starting materials, especially for more complex polycyclic systems, and the electronic requirements of the diene/dienophile partners. This project will investigate the asymmetric diene transmissive pericyclic reactions of dendralenes, which transform simple readily available unsaturated components into structurally complex, enantiomerically enriched polycyclic natural product-like molecules in a single reaction.

Dendralenes (cross conjugated polyenes) participate in complexity generating diene transmissive Diels-Alder (DTDA) reactions. Depending on the substitution pattern of the dendralene and the dieneophile, and whether successive reactions are intermolecular or intramolecular, DTDA reactions can generate a plethora of structurally diverse polycyclic systems, forming two to four rings in one pot, which contain double bonds and stereogengic centres in defined positions. This project aims to expand the scope of the diene transmissive reactivity of dendralenes to include other types of pericyclic reactions. Specifically, this proposal aims to develop asymmetric diene transmissive 6pi-electrocyclisation (6pi-EC)/Diels-Alder (DA) reaction of [3]dendralenes. Such a reaction sequence can generate up to three C-C bonds and two rings, both of which are functionalised with double bonds in defined positions, and up to six defined stereogenic centres, all in one pot. This will enable the concise enantioselective synthesis of highly functionalised polycyclic molecules, including the cores of several classes of biologically active natural products.

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Funding Notes

This project is open to students who can fund their own studies or who have been awarded a scholarship separate from this project. The Chemistry Department at York is pleased to offer Wild Fund Scholarships to new students who will pay tuition fees at the overseas rate. Scholarships are competitive and awarded based on academic ability and financial need. For further information see:

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