Show simple item record

dc.contributor.authorHinze, Meagan
dc.date.accessioned2015-10-15T18:01:57Z
dc.date.available2020-08-17T06:00:58Z
dc.date.issued2015-08-17
dc.identifier.otherbibid: 9255249
dc.identifier.urihttps://hdl.handle.net/1813/40977
dc.description.abstractMarine natural products possess diverse architectures and pharmacology, and have provided scientists with a variety of neurotoxins with the potential to be used as research tools. The nicotinic acetylcholine receptors are ion channels that have been implicated in neurodegenerative diseases and tentatively linked to other processes outside the nervous system. As the pharmacological role and scope of nicotinic acetylcholine receptors becomes more complex and analysis methods improve, natural products with established agonist and antagonist affinities should be periodically reevaluated. The overlooked surugatoxin family of marine toxins is such a case because they can no longer be found in nature. Previously synthesized by Inoue and coworkers, we sought to develop an updated synthetic approach to reestablish access to this fascinating family of natural products. Our original approach focused on utilizing a DielsAlder reaction to form the C-ring with the intention of forming the spirooxindole through an oxidative spirocyclization. Both diene connectivities at the indole C2 and C3 positions were explored but proved unsuccessful. Changing tactics, a direct formation of the spirooxindole ring junction was achieved through lithium halogen exchange and conjugate addition into an unsaturated ketone. , Ultimately, we developed a thirteen-step synthesis to a surugatoxin progenitor (aglycone) via a new oxindole annulation with meta-phenylenediamine and late stage enamine oxidation.!
dc.language.isoen_US
dc.subjectalkaloid
dc.subjectsynthesis
dc.subjectsurugatoxin
dc.titleMarine Natural Product Neurotoxins And The Synthesis Of A Surugatoxin Progenitor
dc.typedissertation or thesis
thesis.degree.disciplineChemistry and Chemical Biology
thesis.degree.grantorCornell University
thesis.degree.levelDoctor of Philosophy
thesis.degree.namePh. D., Chemistry and Chemical Biology
dc.contributor.chairLewis,Chad Arthur
dc.contributor.committeeMemberSchroeder,Frank
dc.contributor.committeeMemberCoates,Geoffrey


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record

Statistics