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Dr Mark Elliott  -  BSc(Hons) CChem MRSC


Our research interests lie in the development of new synthetic methodology, and its application to target synthesis. Key areas include:

Stereoselective annulation reactions of pyrrolidine, oxazoline and thiazoline derivatives which provide access to a range of novel heterobicyclic systems.
Development of new desymmetrisation reactions of cyclohexadiene systems to provide highly complex carbocyclic and heterocyclic systems.

Recent highlights include the total synthesis of batzelladine C methyl ester 2 from succinimide 1, permitting the stereochemical assignment of this challenging natural product.

Lycoposerramine A is a complex alkaloid featuring a pentacyclic core with five stereogenic centres and an unprecedented (in natural products) spirocyclic oxadiazolidinone ring. Compound 4 was prepared in only 7 steps from cyclohexadiene 3 as a highly functionalised model for this core.

A further application of cyclohexa-1,4-diene chemistry is shown in the highly efficient Prins desymmetrisation of compound 5 to give product 6 which is structurally and stereochemically related to the cladiellin diterpenes.

One final highlight from our recent work is the conversion of alkylidenepyrroldine 7 into the adduct 8. This reaction proceeds by a one-pot multistep sequence involving trapping of the nitrous acid that is liberated from the nitrolic acid, followed by decarboxylation and two dipolar cycloadditions (collaboration with Prof. Yasar Dürüst, Abant Izzet Baysal University, Turkey).

Diagram