Total Synthesis of (-)-Spiroleucettadine
|dc.contributor.author||Lamb, Richard Alastair|
|dc.identifier.citation||Lamb, R. A. (2018). Total Synthesis of (-)-Spiroleucettadine (Thesis, Doctor of Philosophy). University of Otago. Retrieved from http://hdl.handle.net/10523/8072||en|
|dc.description.abstract||One 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.publisher||University of Otago|
|dc.rights||All 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.title||Total Synthesis of (-)-Spiroleucettadine|
|thesis.degree.name||Doctor of Philosophy|
|thesis.degree.grantor||University of Otago|
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