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Wednesday, April 22 • 9:40am - 10:00am
Synthetic Strategies Towards Indole Analogues of a Tamoxifen® Metabolite

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The target indole analogue of 4-hydroxy Tamoxifen® is of interest due to its theoretically increased affinity for the estrogen receptor relative to the popular breast cancer treatment, Tamoxifen®. The Hemetsberger-Knittel indole synthesis methodology has been proven to be an effective and efficient procedure to synthesize substituted indoles from vinyl azides. The use of substituted benzophenones in producing vinyl azides would provide an efficient route to aryl substituted indoles and the series of indole analogues of 4-hydroxy Tamoxifen® desired in this project. Unfortunately, the low reactivity and greater steric hindrance of benzophenone compared to benzaldehydes hindered this process. The Hemetsberger-Knittel indole methodology was then employed to generate the desired methoxyindole core followed by bromination at the 3-position of the indole. This allows for the addition of the aryl group via a Sonogashira coupling. The alternative but effective route will be discussed along with the progress toward an indole analogue of Tamoxifen®.


Wednesday April 22, 2015 9:40am - 10:00am PDT
123 Zeis Hall

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