Page 6 - PERIODIC Magazine Issue 7
P. 6

N       ew research

              Science Writer Ashley Tsai reports on some of the new and exciting research
              from the Department of Chemistry over the past year.

              Anderson group                                  For Marie, working with Pfizer provided insightful
                                                              industry perspectives and resources: “I enjoyed looking
              Synthesis of α-chiral BCPs                      at the project’s academic novelty and also its commercial
                            It doesn’t look like it should exist,   viability and applicability. Getting input on my project
                            but it does. Consisting of five carbon   from both an academic and industrial point of view was
                            atoms, bicyclo[1.1.1]pentanes (BCPs)   extremely valuable.”
                            are an intriguing three-dimensional   The synthesis and evaluation of BCP compounds are
                            chemical structure not found in nature.   an active area of research, and the Anderson group
                            Pharmaceutical and materials scientists   continues to develop methods to further explore their full
                            are increasingly interested in BCPs due   potential.
                            to their ability to act as both a surrogate   Reference: Wong, M.L.J.; Mousseau, J.J.; Mansfield, S.J.; Anderson, E.A.;
                            for certain functional groups and a   Synthesis of enantioenriched α-chiral bicyclo[1.1.1]pentanes, Org. Lett. 2019,
                            well-defined spacer unit.         21, 2408-2411, (doi: 10.1021/acs.orglett.9b00691).
                            Marie Wong, a DPhil candidate
                            co-supervised by Professor Ed
                            Anderson and Dr. James J. Mousseau
                            from Pfizer, has developed an efficient
          Professor Ed Anderson and
          Marie Wong        method to synthesise BCPs with
                            an adjacent stereocenter (α-chiral
              BCPs). The partnership arose from the Synthesis for
              Biology & Medicine Centre for Doctoral Training (CDT),
              which trains graduate students by combining expertise
              from academia and industry to solve interdisciplinary
              Stereoisomers, molecules which have the same
              chemical groups and connectivities but differ in their
              spatial configurations, are critical in pharmacology. It is   The Anderson group developed an efficient method to
              estimated that over half of all drugs in current use are   synthesise α-chiral BCPs with a wide range of substituents.
              chiral (feature three-dimensional stereoisomerism), and
              the different forms can result in considerably distinct
              toxicology, pharmacokinetics, metabolism and so on.
              That is because biological molecules themselves are
              often chiral, and distinguish between the different forms.
              The Anderson group was able to synthesise α-chiral
              BCPs with a wide range of substituents through highly
              selective enolate reactions, including alkylation,
              halogenation, oxygenation and amination. Importantly,
              the atom transfer radical addition used to install the BCP
              unit is an efficient method to access these compounds in
              high yields using milder conditions compared to previous
              procedures. The group successfully applied their method   The Anderson group used an atom transfer radical addition to
              to pharmaceuticals by synthesising a BCP analogue   synthesise α-chiral BCPs with high yields and mild conditions.
              of tarenflurbil, a stereo-specific version of the NSAID

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