eprintid: 19354
rev_number: 19
userid: 2399
dir: disk0/00/01/93/54
datestamp: 2013-09-22 19:25:43
lastmod: 2016-11-15 14:14:15
status_changed: 2013-09-22 19:25:43
type: thesis_degree
metadata_visibility: show
contact_email: anthonyfbencivengawork@gmail.com
item_issues_count: 0
eprint_status: archive
creators_name: Bencivenga, Anthony
creators_email: afb19@pitt.edu
creators_id: AFB19
title: PROGRESS IN THE TOTAL SYNTHESIS OF SPIROLIDE C AND A MODEL SYSTEM OF A KEY DIELS-ALDER MACROCYCLIZATION
ispublished: unpub
divisions: sch_as_chemistry
full_text_status: public
keywords: spirolide c
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.
date: 2013-09-22
date_type: published
pages: 60
institution: University of Pittsburgh
refereed: TRUE
etdcommittee_type: committee_chair
etdcommittee_type: committee_member
etdcommittee_type: committee_member
etdcommittee_name: Nelson, Scott G
etdcommittee_name: Floreancig, Paul
etdcommittee_name: Curran, Dennis P
etdcommittee_email: sgnelson@pitt.edu
etdcommittee_email: florean@pitt.edu
etdcommittee_email: curran@pitt.edu
etdcommittee_id: SGNELSON
etdcommittee_id: FLOREAN
etdcommittee_id: CURRAN
etd_defense_date: 2013-07-15
etd_approval_date: 2013-09-22
etd_submission_date: 2013-07-17
etd_release_date: 2013-09-22
etd_access_restriction: immediate
etd_patent_pending: FALSE
thesis_type: thesis
degree: MS
citation:   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    (Unpublished)  
document_url: http://d-scholarship-dev.library.pitt.edu/19354/1/Progress_in_the_Total_Synthesis_of_Spirolide_C_and_a_Model_System_of_a_Key_Diels-Alder_Macrocyclization.pdf