We are engaged in a program to develop neuroprotective agents based on the structure of a natural product known as vitisinol D, which contains a unique bridged bicyclic core. From this effort, an analog, known as fly2, was identified as a potent neuroprotectant using a fruit fly model (<i>Drosophila melanogaster</i>). In this presentation, we report the optimized synthesis of a close analog of fly2, one that lacks a methyl substituent. This analog possesses nearly identical bioactivity as fly2; however, it can be produced in higher yield, thus making possible late-stage diversification. Using the optimized route, new analogs of des-methyl-fly2 have been prepared. Synthesis and optimization details will be described along with bioactivity results for several bicyclic compounds.

Synthesis and optimization of [3.2.1] bicyclic compounds as potential neuroprotective agents

256th National Meeting (2018)

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