Document Type


Date of Degree

Fall 2011

Degree Name

PhD (Doctor of Philosophy)

Degree In


First Advisor

Wiemer, David F

First Committee Member

Wiemer, David F

Second Committee Member

Gloer, James B

Third Committee Member

Arnold, Mark A

Fourth Committee Member

Pigge, F Christopher

Fifth Committee Member

Olivo, Horacio F


Cancer is a serious family of disease that continues to cripple and claim those afflicted. 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 with the hope of finding naturally occurring compounds that can successfully combat cancer. Presently, 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 one family of natural products uncovered by the NCI that is being explored for chemotherapeutic applications, namely the schweinfurthins. The schweinfurthins were isolated by the NCI; however the natural source, Macaranga schweinfurthii, did not provide these compounds in ample quantity 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, describes the synthesis of numerous structural analogues, and details advances to the field of cascade cyclizations which makes their synthesis possible.


Antiproliferative Agent, Anti-Proliferative Agent, Cascade Cyclization, Natural Product, Schweinfurthin, Total Synthesis


1, xiv, 222 pages


Includes bibliographical references (pages 189-193).


Copyright 2011 Joseph John Topczewski

Included in

Chemistry Commons