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PROGRESS IN THE TOTAL SYNTHESIS OF SPIROLIDE C AND A MODEL SYSTEM OF A KEY DIELS-ALDER MACROCYCLIZATION

Bencivenga, Anthony (2013) PROGRESS IN THE TOTAL SYNTHESIS OF SPIROLIDE C AND A MODEL SYSTEM OF A KEY DIELS-ALDER MACROCYCLIZATION. Master's Thesis, University of Pittsburgh. (Unpublished)

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Abstract

Spirolode C is a macrocyclic marine toxin produced by the dinoflagellate Alexandrium ostenfeldii that has attracted significant synthetic interest due in particular to its rare spirocyclic imine fragment. The work presented herein details progress made in the synthesis of a model system that will be used to optimize reaction conditions for a biomimetic macrocycle closing Diels-Alder reaction in our planned total synthesis. The synthesis of the model system required an extension of our isomerization/Claisen rearrangement (ICR) to be compatible with new vinyl bromide-containing substrates. New conditions to affect the ICR of these challenging substrates were successfully developed, and this led to significant progress in the synthesis of the desired model system.


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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Bencivenga, Anthonyafb19@pitt.eduAFB19
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairNelson, Scott Gsgnelson@pitt.eduSGNELSON
Committee MemberFloreancig, Paulflorean@pitt.eduFLOREAN
Committee MemberCurran, Dennis Pcurran@pitt.eduCURRAN
Date: 22 September 2013
Date Type: Publication
Defense Date: 15 July 2013
Approval Date: 22 September 2013
Submission Date: 17 July 2013
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 60
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: spirolide c
Date Deposited: 22 Sep 2013 19:25
Last Modified: 15 Nov 2016 14:14
URI: http://d-scholarship.pitt.edu/id/eprint/19354

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