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Studies in Natural Product Chemistry: Synthesis of Palmarumycin CP1 Analogs and Total Synthesis and Structure Validation of (+)-Bistramide C

Hopkins, Tamara Denise (2005) Studies in Natural Product Chemistry: Synthesis of Palmarumycin CP1 Analogs and Total Synthesis and Structure Validation of (+)-Bistramide C. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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The first chapter describes our preparation of novel analogs of the natural product, palmarumycin CP1. Several derivatives demonstrated potent and selective inhibition of thioredoxin and thioredoxin reductase as well as antiproliferative activity against MCF-7 and MDA-MB-231 human breast cancer cell lines. Furthermore, we also made progress towards the synthesis of the structurally related naphthalenediol spiroacetal natural product, spiroxin C. We developed efficient, facile syntheses for the preparation of the two building blocks required for the key Ullmann ether coupling reaction.The second chapter details the asymmetric total synthesis of the Lissoclinum bistratum natural product, bistramide C. Our synthetic route featured a highly-convergent three-component coupling strategy for the final assembly of the target molecule. In addition, our total synthesis highlighted our MAO-mediated, chiral zirconocene-catalyzed methylalumination of terminal olefins, a tandem BiBr3-initiated cyclization-allylation for the formation of a 2,6-trans-substituted pyran and hypervalent iodine-promoted spiroketalization. The spectroscopic properties (i.e. 1H and 13C NMR, [alpha]D, CD) of the synthetic material were in very close agreement to the measurements of an authentic sample of the natural product. Thus, our synthetic efforts in conjunction with NMR methodology and chiroptical tools culminated in the first total synthesis of (+)-bistramide C.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Hopkins, Tamara
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberDay, Billybday@pitt.eduBDAY
Committee MemberWilcox, Craigdaylite@pitt.eduDAYLITE
Committee MemberFloreancig, Paulflorean@pitt.eduFLOREAN
Date: 4 October 2005
Date Type: Completion
Defense Date: 11 August 2005
Approval Date: 4 October 2005
Submission Date: 23 August 2005
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: cyclic polyethers; spirobisnaphthalenes; van't Hoff
Other ID:, etd-08232005-230211
Date Deposited: 10 Nov 2011 20:00
Last Modified: 15 Nov 2016 13:49


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