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Saturday, April 1, 2023

Fast entry to molecular complexity from bioderived 5-HMF derivatives by way of cascade cycloadditions


For the primary time, the transformation of biobased 5-HMF derivatives succeeded in a 2 × [4 + 2] cascade cycloaddition response, resulting in a drastic (3–5-fold) enhance in molecular complexity because of one artificial step. A brand new method to using plant biomass in natural synthesis utilizing a cascade Diels–Alder response of 5-HMF dimer derivatives with alkynes has been developed. This response proceeds beneath thermodynamic management, diastereoselectively and regioselectively, offering fast entry to compounds of excessive molecular complexity with the identical artificial availability as beforehand obtained common cycloadducts. As an idea illustration, beneath situations of kinetic management, cycloadditions of two molecules of dienophiles are realized, and the ensuing merchandise, when heated, rearrange into thermodynamically extra favorable cascade merchandise. Response pathways had been studied intimately utilizing quantum chemical calculations to disclose main components influencing the selectivity of the method. Discovery of a brand new sustainability pathway needs to be famous – up to now, oligomeric derivatives are thought of a waste of 5-HMF degradation, whereas the current research highlights them as a helpful materials for the synthesis of nonplanar scaffolds.

Graphical abstract: Rapid access to molecular complexity from bioderived 5-HMF derivatives via cascade cycloadditions

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