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Towards the Total Synthesis and Stereochemistry Determination of Stresgenin B

Cook, Michael (2016) Towards the Total Synthesis and Stereochemistry Determination of Stresgenin B. Master's Thesis, University of Pittsburgh. (Unpublished)

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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Status: Unpublished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:
CreatorsEmailPitt UsernameORCID
Cook, Michaelmpc58@pitt.eduMPC58
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairKoide, Kazunorikoide@pitt.eduKOIDE
Committee MemberWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberWilcox, Craigdaylite@pitt.eduDAYLITE
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 Jan 2017 15:06
URI: http://d-scholarship.pitt.edu/id/eprint/29241

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