Cook, Michael
(2016)
Towards the Total Synthesis and Stereochemistry Determination of Stresgenin B.
Master's Thesis, University of Pittsburgh.
(Unpublished)
Abstract
The natural product stresgenin B has been shown to inhibit the up-regulation of HSPs in vivo. Since HSPs are known to protect cancerous cells from a variety of internal and applied stress (such as drug treatments and radiation), this makes stresgenin B a potentially new chemotherapeutic agent.
Herein is described the development and application of a new synthetic method that efficiently installs a primary amide-bearing acetonide group. Based on extensive Reaxys and SciFinder searching, we have found this to be only the second example of such a moiety, and the first in the class of 5,5-bicyclic systems. This methodology has the potential to be expanded to include esters, carboxylic acids, and other more exotically functionalized acetonides. In addition, we have held in reserve analogous compounds (synthesized during the course of this work), very similar in structure and composition to the natural product, for future SAR studies.
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Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
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| Date: |
20 September 2016 |
| Date Type: |
Publication |
| Defense Date: |
4 April 2011 |
| Approval Date: |
20 September 2016 |
| Submission Date: |
10 August 2016 |
| Access Restriction: |
5 year -- Restrict access to University of Pittsburgh for a period of 5 years. |
| Number of Pages: |
129 |
| Institution: |
University of Pittsburgh |
| Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
| Degree: |
MS - Master of Science |
| Thesis Type: |
Master's Thesis |
| Refereed: |
Yes |
| Uncontrolled Keywords: |
Stresgenin B
Synthesis
Natural Product
HSP |
| Date Deposited: |
20 Sep 2016 14:51 |
| Last Modified: |
20 Sep 2021 05:15 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/29241 |
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