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Kristen Gardner is a third year PhD Candidate in Chemistry at the University of California, Berkeley, where she is a Chancellor’s Fellow and NSF Graduate Research Fellow. As a member of Prof. Richmond Sarpong’s Group, she studies new methods to access heterocyclic ring scaffolds and works on the total synthesis of cephalotane-type diterpenoids. Kristen graduated with a BS in chemistry with honors and distinction in 2019 from the University of North Carolina at Chapel Hill and was awarded the Francis P. Venable Medal, the highest distinction given by the chemistry department. As a Chancellor’s Science Scholar at UNC, she studied cation-controlled olefin isomerization by palladium complexes under the advisement of Prof. Alex Miller. Outside of the lab, she is dedicated to teaching the next generation of scientists, as made evident by the Outstanding Graduate Student Instructor awarded in her first semester at Berkeley, and in particular, wants to create a more inclusive environment and help other underrepresented scientists find their place and their voice.

Progress Towards the Diversification of 2-pyrones

The versatility of 2-pyrones in ring-forming processes has been explored for almost a century. Direct pericyclic annulations of 2-pyrones, such as [4+2]-cycloadditions and 4π electrocyclizations, have proven to be effective tactics for accessing synthetically versatile bicycles that have been applied to the total synthesis of a variety of natural products. Alternatively, the Sarpong Group has developed novel annulation strategies, enabled by the nucleophilic 1,6- and 1,2-ring opening of 2-pyrones, to access a myriad of ring systems. Our continued efforts focus on expanding the scope of this versatile pyrone remodeling strategy to expand the diversity of scaffolds that can be obtained from 2-pyrone. Our most recent work focused on exploiting the 1,2-ring opening of functionalized 2-pyrones as a general strategy for synthesizing diverse N-heterocycles. This approach entails cross-coupling a nitrogen-containing heterocycle followed by a selective 1,2-ring opening of the resulting adducts with NaOMe, and an annulation to form the new heterocycle. This method was applied to the formal total synthesis of three natural products in the fascaplysin family. Additionally, novel syntheses of substituted benzoates using Rh-mediated Hopf cyclizations and syntheses of substituted aromatic rings at room temperature will be discussed. Overall, these diverse, but complementary, transformations set the stage to further diversify 2-pyrones into various carbo- and heterocyclic ring systems and will find widespread application in natural product synthesis.

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