Conventional bio-derived polymers such as polylactide (PLA) are desirable due to the fact that they are bio-renewable and biodegradable. However, PLA does have a shortcoming: its functionality makes it hydrophobic and thus slow to breakdown. This hinders its applications. As a result, it is necessary to create new ways to synthesize and produce functionalized PLA materials that use biologically appropriate monomers. To address this problem, we are interested in developing a method to synthesize a C5 functionalized lactone—3,6-dihydro-2H-pyran-2-one—from C5-rich hydrozylate. The C5 cyclic ester is synthesized from L-arabinose and D-Xylose which are sugars that can be obtained from Brown-Forman’s dried distiller’s grain (DDG). The method for producing the lactone comes from a series of known reactions. However, majority of the work done focuses on the optimization of step 3 (the glycal synthesis). Additionally, no work has been done on the ring opening capacity of the cyclic ester. We believe that the unconjugated double bond in the lactone will allow for this possibility and enable us to create new materials with different properties. This will be addressed after successful completion and optimization of the overall synthesis.

Multistep synthesis of the biocompatible lactone 3,6-dihydro-2H-pyran-2-one

249th National Meeting (2015)

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