We have previously established a synthesis route towards all-carbon [3.2.1] bridged bicycles that we have termed “resveramorphs” or “RVMs” since their structures were inspired by a resveratrol natural product known as vitisinol D. These novel compounds were found to possess potent neuroprotective properties against oxidative stress. In our current six-step synthesis route there involves the conversion of an enol lactone to a bridged bicycle under reducing conditions using a Lewis acidic reducing agent (e.g., diisobutyl aluminum hydride). Our current hypothesis is that the chelating reducing agent both facilitates ring closure and blocks one face of the molecule to afford a highly diastereoselective outcome. However, this transformation, pioneered in our group, currently gives low yields primarily due to the formation of unwanted overreduction products and therefore represents a bottleneck to our medicinal chemistry investigation. In this presentation, we discuss our evaluation of key reaction parameters and explain how these were used to refine our current mechanism understanding of this intriguing bicyclization step.

Resveratrol-natural product inspired neuroprotective agents: An optimized route to all-carbon [3.2.1] bridged bicyclic compounds via a reductive aldol step

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ACS Fall 2022

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