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Synthetic approach to isogemichalcone C A potential aromatase inhibitor

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Description: The research presented here focuses on the synthesis of isogemichalcone C ( 27 ). This natural product, derived from the mulberry tree, is a potent aromatase inhibitor. The inhibition of aromatase has been shown to be a useful method for the treatment for breast cancer. The synthesis of morachalcone A ( 29 ), a derivative of isogemichalcone C, had been completed utilizing a 1,3 prenyl rearrangement to deliver the C -prenylated aryl ring within morachalcone A. The route was not adaptable to the synthesis of related esterified aromatase inhibitors as originally thought; therefore, a new route was designed to produce the natural product of interest here. The current synthetic approach to isogemichalcone C revolves around a Stille coupling that would create the carbon-carbon bond linking an allyl group with an aryl ring. At this time, there is evidence that an appropriately substituted Stille reaction has occurred between a model benzyl bromide 105 and vinylstannane 94. Future trials will continue in order to optimize the reaction conditions as well as to incorporate benzyl bromide 85 so that the synthesis directed toward isogemichalcone C can continue. This work has demonstrated a variety of coupling techniques, as well as an improvement in the formation of the esterified natural product, isogemichalcone C.
Language: English
Format: Degree Work