Authors:

Riley N Brown

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About Paper:

Dihydro-beta-agarofurans are a class of eudesmane terpene natural products demonstrating potent biological activities ranging from reversing multi-drug efflux, anti-inflammatory effects, anti-cancer and tumor suppression abilities. Isolating this class of natural products from natural sources is low yielding hindering the full in vitro and in vivo exploration of their capabilities. A synthetic approach to their preparation, capable of producing material in quantities necessary for biological study would enable mechanistic research into their pharmacology. The authors have established a concise diastereoselective route to the octalin core, solving the key stereotriad problem on a meso-substrate through consecutive alkoxy anion-directed conjugate additions followed by ring-closing metathesis. This product is then subjected to an Iridium-mediated photoredox acyl cyclization followed by Grignard addition and subsequent closure to form the tetrahydrofuran ring that is characteristic of the dihydro-beta-agarofuran family. From this point, preparation of 2-3 natural products with anti-cancer and tumor suppression abilities will be synthesized. All intermediates and products will be analyzed by both hydrogen and carbon NMR spectroscopy, and mass spectrometry to confirm their structure. Keywords: Natural Products; Biological Activity; Total Synthesis

Source:

Purdue University / 2024

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Co-authors:

Riley N Brown