Abstract
The target indole analogue of 4-hydroxy Tamoxifen® is of interest due to its theoretically increased because it has been hypothesized to have binding affinity for the estrogen receptor relative to the popular breast cancer drug, Tamoxifen®. The Hemetsberger-Knittel indole synthesis methodology has proven to be an effective and efficient procedure to produce substituted indoles from vinyl azides. The use of substituted benzophenones in producing vinyl azides would provide the most efficient route to aryl substituted indoles and the series of analogs 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 would allow for the addition of the aryl group via a Kumada coupling. The alternative but efficient route will be discussed along with the progress toward an indole analogue of Tamoxifen®.
How to Cite
Long, M., (2015) “Synthetic Strategies Towards Indole Analogues of a Tamoxifen® Metabolite”, Capstone, The UNC Asheville Journal of Undergraduate Scholarship 28(1).
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