NYU's Janice Cutler Professor of Chemistry Dirk Trauner and his colleagues published a biomimetic total synthesis of the natural product preuisolactone A in the Journal of the American Chemical Society (September 2019). They synthesized the highly complex natural product in a mere three steps, and through their synthesis were able to show that preuisolactone A is likely a polyketide, and not a terpenoid, as previously thought. Trauner group graduate students Alexander Novak and NYU REU student Claire Grigglestone worked on the study called "A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A". Their synthesis has also been highlighted by Chemical & Engineering News here.
Abstract: A short, biomimetic synthesis of the fungal metabolite preuisolactone A is described. Its key steps are a purpurogallin-type (5 + 2)-cycloaddition, followed by fragmentation, vinylogous aldol addition, oxidative lactonization, and a final benzilic acid rearrangement. Our work explains why preuisolactone A has been isolated as a racemate and suggests that the natural product is not a sesquiterpenoid but a phenolic polyketide.
This research was supported by the National Institutes of Health and the National Science Foundation through funding of the REU Site for Chemical Biology at New York University.