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(Unpublished)
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
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Status: |
Unpublished |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID |
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Bencivenga, Anthony | afb19@pitt.edu | AFB19 | |
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ETD Committee: |
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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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