Synthetic efforts toward a total synthesis of (+)-Pelorusdie A.

Loading...
Thumbnail Image

Persistent link to this item

Statistics
View Statistics

Journal Title

Journal ISSN

Volume Title

Title

Synthetic efforts toward a total synthesis of (+)-Pelorusdie A.

Alternative title

Published Date

2009-06

Publisher

Type

Thesis or Dissertation

Abstract

This thesis has been divided into six chapters that describe synthetic efforts toward the cytotoxic marine macrolide (+)-peloruside A, isolated by Northcote and coworkers from the New Zealand marine sponge Mycale hentscheli. Chapter 1 discusses the background of peloruside A and published literature studies relating to its biological activity. Chapter 2 conveys a detailed report of the synthetic efforts by others that have resulted in three total syntheses and multiple efforts toward the total synthesis of peloruside A. Chapter 3 describes the previous synthetic efforts by Hoye group members toward peloruside A. Two different strategies for synthesizing the C13-C20 fragment of (+)-peloruside A have been established using ring-closing metathesis. Synthesis of the C1-C9 fragment of (+)-peloruside A was accomplished using a kinetic lactonization strategy. Chapter 4 reports on my efforts at scaling-up and optimizing the synthesis of the C1-C9 fragment of (+)-peloruside A and modifications to the previous route. Chapter 5 describes the new progress toward synthesizing (+)-peloruside A that was achieved. These efforts culminated in the synthesis of a C1-C11 fragment of (+)-peloruside A along with studies investigating the coupling of late stage segments via a 1,5-anti boron-mediated aldol. Chapter 6 highlights the key features of my synthetic efforts toward (+)-peloruside A.

Description

University of Minnesota Ph.D. dissertation. June 2009. Major: Chemisrty. Advisor: Thomas R. Hoye. 1 computer file (PDF); xi, 342 pages, appendix A.

Related to

Replaces

License

Collections

Series/Report Number

Funding information

Isbn identifier

Doi identifier

Previously Published Citation

Other identifiers

Suggested citation

Kopel, Lucas C.. (2009). Synthetic efforts toward a total synthesis of (+)-Pelorusdie A.. Retrieved from the University Digital Conservancy, https://hdl.handle.net/11299/54537.

Content distributed via the University Digital Conservancy may be subject to additional license and use restrictions applied by the depositor. By using these files, users agree to the Terms of Use. Materials in the UDC may contain content that is disturbing and/or harmful. For more information, please see our statement on harmful content in digital repositories.