Please join Yale Chemistry for a thesis seminar with Rachel Cantrell, Newhouse Lab.
Title: Divergent Syntheses of Clovane and Aminosterol Natural Products and Analogs
Summary: I’ll be discussing my work on the ML-guided synthesis of clovan-2,9-dione, rumphellclovane B, and canangaterpene II natural products, as well as the generation of analogs and examination of other substrates to synthetically validate the ML model. I’ll also be explaining our current routes towards the synthesis of trodusquemine and how we’re accessing previously unexplored unnatural stereocenters. As the main strategy hinges on a challenging HWE reaction, various approaches have been used to generate functionalized phosphonate esters in an effort to increase route efficiency. The application of cHAT to a key intermediate in our route to trodusquemine is detailed as well, and the results of screening a variety of thiol cocatalysts is discussed. Current focus lies on the full characterization of the natural product to confirm its formation, as well as development of a replicable purification technique to separate the C20 diastereomers via semi-preparatory HPLC.
