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Cascade cyclizations and the schweinfurthins

Posted on:2012-09-24Degree:Ph.DType:Thesis
University:The University of IowaCandidate:Topczewski, Joseph JohnFull Text:PDF
GTID:2451390008498021Subject:Chemistry
Abstract/Summary:
For the last several decades, America has invested in a national program to alleviate cancer and cancer-related suffering, ultimately seeking a cure. As part of this goal, the National Cancer Institute (NCI) has spent significant effort scouring the globe to find naturally occurring compounds that can successfully combat cancer. This effort has uncovered many natural products with chemotherapeutic potential and many of the lead agents used in the fight against cancer are either natural products themselves or are compounds inspired by a natural product.;This work describes the synthesis of one family of natural products uncovered by the NCI that is being explored for chemotherapeutic applications, namely the schweinfurthins. The schweinfurthins were isolated from the plant Macaranga schweinfurthii but the natural source did not provide these compounds in a quantity sufficient to permit further study. The paucity of natural material indicated that a chemical synthesis of these compounds would be the most reliable method to provide meaningful amounts of schweinfurthins. The present work describes the chemical synthesis of four of the most potent schweinfurthins, reports the synthesis of numerous structural analogues, and details advances to the field of cascade cyclizations which makes their synthesis possible.
Keywords/Search Tags:Schweinfurthins, Synthesis, Cancer
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