Having the ability to selectively modify any position of a complex molecular scaffold without the use covalent directing or protecting groups is a major goal of organic synthesis.
We are a synthetic organic chemistry group that is interested in leveraging bio-inspired molecular recognition and non-covalent O–H/N–H/C–H bond polarization to develop new catalysts for precision functionalization of complex molecules.
leveraging molecular recognition interactions from nature to design catalysts for precision editing of complex molecules
harnessing new strategic disconnections to access natural products for biological evaluation and derivatization
developing small molecule reagents for monomer-selective bioconjugation of complex biological glycans
Molecules like sugars, glycans and highly oxidized natural products are topologically and stereochemically complex, but lack diverse functional handles that can be distinguished on the basis of chemoselectivity. This feature presents an unmet synthetic challenge, as it precludes the targeted, direct modification of such species. Historically, orthogonal protecting group strategies or iterative oxidation schemes have been employed to synthesize or modify these molecules. We will be focused on designing new strategies for the direct and site-selective C–H and O–H activation of these highly oxidized molecules by taking advantage of bioinspired molecular recognition.
The resulting species will be used for catalysis, allowing for the precision molecular editing of structures that are topologically and stereochemically complex, but functionally homogenous. We will apply these catalysts to access new disconnections for natural products total synthesis, to directly derivatize carbohydrate-derived building blocks such as biomass degredation products, polyol desymmetriztion and monomer-selective glycan bioconjugation.