@unpublished{pittir19354, month = {September}, title = {PROGRESS IN THE TOTAL SYNTHESIS OF SPIROLIDE C AND A MODEL SYSTEM OF A KEY DIELS-ALDER MACROCYCLIZATION}, author = {Anthony Bencivenga}, year = {2013}, keywords = {spirolide c}, url = {http://d-scholarship-dev.library.pitt.edu/19354/}, 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.} }