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dc.contributor.advisorHawkins, Bill
dc.contributor.authorLamb, Richard Alastair
dc.date.available2018-06-05T00:02:31Z
dc.date.copyright2018
dc.identifier.citationLamb, R. A. (2018). Total Synthesis of (-)-Spiroleucettadine (Thesis, Doctor of Philosophy). University of Otago. Retrieved from http://hdl.handle.net/10523/8072en
dc.identifier.urihttp://hdl.handle.net/10523/8072
dc.description.abstractOne of a number of intriguing new alkaloids isolated from the Leucetta sp. sponge in 2004, spiroleucettadine displayed unique structural features on a restricted scaffold: a trans-fused 5,5-bicyclic ring system together with an amino hemiketal moiety. Attempts to synthesize the initially proposed structure failed, raising questions as to its veracity, and structure revision ensued in 2008; no successful synthetic approach has been reported to date. Herein, we describe the enantiospecific total synthesis of (-)-spiroleucettadine by a highly efficient biomimetic inspired approach starting from L-tyrosine. One of two key hypervalent-iodine-mediated oxidation reactions forged the spirocyclic center, and the other enabled the installation of the methylamine side chain in the penultimate step. Our approach provides synthetic access to a new class of spiroannulated natural products and will enable future studies of the structure–biological-activity relationships of these antibacterial compounds.
dc.language.isoen
dc.publisherUniversity of Otago
dc.rightsAll items in OUR Archive are provided for private study and research purposes and are protected by copyright with all rights reserved unless otherwise indicated.
dc.subjectleucetta
dc.subjectalkaloid
dc.subjecttotal
dc.subjectsynthesis
dc.subjectspiroleucettadine
dc.subjectnatural
dc.subjectproduct
dc.titleTotal Synthesis of (-)-Spiroleucettadine
dc.typeThesis
dc.date.updated2018-06-04T23:25:12Z
dc.language.rfc3066en
thesis.degree.disciplineChemistry
thesis.degree.nameDoctor of Philosophy
thesis.degree.grantorUniversity of Otago
thesis.degree.levelDoctoral
otago.interloanyes
otago.openaccessAbstract Only
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