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Synthetic Studies on Cycloclavine, Cyclopiazonic Acid, and Other Biologically Active Indole-Containing Compounds

Petronijevic, Filip (2012) Synthetic Studies on Cycloclavine, Cyclopiazonic Acid, and Other Biologically Active Indole-Containing Compounds. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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The first section of this dissertation describes the synthesis of five indole-containing compounds used in the BoNT LC (botulinum neurotoxin light chain) SAR analysis. Our approach employs a Pd(II)-catalyzed cyclization for the formation of indole rings, which are subsequently converted to the corresponding amidines or imidazolines.
The second section describes the extension of the indole synthesis methodology through a microwave assisted IMDAF (intramolecular Diels-Alder furan) reaction. This protocol allows for a convergent and rapid preparation of 4-mono- and 3,4-disubstituted indoles. This cascade process is quite tolerant of functional groups and associated substitution patterns.
The third part we describes novel routes to the naturally occurring indole alkaloid cycloclavine and its unnatural C(5)-epimer. Key features include the rapid construction of the heterocyclic core segments by two Diels-Alder reactions. An indole annulation was accomplished by a late-stage IMDAF reaction, while the cyclopropa[c]indoline core of cycloclavine was derived through a stereoselective intramolecular [4+2] cycloaddition of a methylenecyclopropane.
The forth section describes an approach towards the total synthesis of cyclopiazonic acid. A promising route to this alkaloid was established, including a rapid construction of the tricyclic indole-containing core and a stereoselective pyrrolidinone ring formation.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Petronijevic, Filipfrp4@pitt.eduFRP4
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberNelson, Scottsgnelson@pitt.eduSGNELSON
Committee MemberCurran, Denniscurran@pitt.eduCURRAN
Committee MemberDay, Billybday@pitt.eduBDAY
Date: 2 October 2012
Date Type: Publication
Defense Date: 23 May 2012
Approval Date: 2 October 2012
Submission Date: 4 June 2012
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 265
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: Indole, Cycloclavine, IMDAF, Cyclopiazonic Acid
Date Deposited: 02 Oct 2012 15:52
Last Modified: 15 Nov 2016 13:58


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