Synthetic Methodology

We are interested in novel processes that form strategic carbon-carbon or carbon-heteroatom bonds, assemble challenging ring systems, and establish new stereocentres. A related goal is to link two or more sequenced bond-forming reactions in tandem, leading to “domino processes” that accomplish a large build-up in molecular complexity in a single synthetic transformation. While pursuing these objectives, we try to identify underutilized classes of high-energy reactive intermediates that may be harnessed for novel types of reactions.

Currently, we are working within three different areas of synthetic methodology: Further development of the Nazarov reaction as well as different approaches to trap its oxy-allyl cation intermediate. Metallocarbenes and the cyclic ylides derived from their addition to pendant heteroatoms are reactive intermediates that attract our interest as useful synthetic intermediates. Finally, photochemical reactions for accomplishing otherwise elusive synthetic transformations, were the photochemical crossed [4+4]-cycloaddition has been in particular focus.

Target-Directed Synthesis

Total synthesis works in tandem with synthetic methodology, by identifying problems that require new methodology and by providing a complex setting to test the generality of a new method. Based on the synthetic methods described above, we are currently engaged in the total synthesis of five different target molecules, Dactylol, Phorbol, Taxinine, Traversinal and 7,8-Epoxy-4-basemen-6-one. In four of those the recurrent theme is the presence of a cyclooctane ring, and Phorbol is a tetracycle consisting of a 5-7-6-3 ring system.

Biorefining Conversions

One of the principal challenges faced in utilization of biomass for the production of platform chemicals is the need to reductively convert highly oxidized materials. To address these shortcomings, novel approaches to the deoxygenation of biomass-derived polyols by chemical conversion will be investigated. This will be a proof-of-principle project, designed to identify optimal conditions for carrying out deoxygenation of glycerol and higher polyols with reduced energy input. Optimized conditions will then be applied using glycerol produced by an industrial bioconversion plant or other carbohydrate-rich feedstock.

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