Page 6 - PERIODIC Magazine Issue 7

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
challenges.
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
flurbiprofen.

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Periodic The Magazine of the Department of Chemistry