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dc.contributor.advisorBayer, Annette
dc.contributor.advisorHansen, Jørn H
dc.contributor.advisorEngqvist, Magnus
dc.contributor.authorGuttormsen, Yngve
dc.date.accessioned2015-05-15T10:18:34Z
dc.date.available2015-05-15T10:18:34Z
dc.date.issued2014-05
dc.description.abstractThe Breitfussins are a series of closely related heterocyclic compounds originated from the marine organism Thelia Breitfussi. The core is a 5(indol-3-yl)-2-(pyrrol-2-yl)oxazole, which has not been observed prior to its isolation in 2007. The divergence of the Breitfussins lies in the halogenation pattern and methoxy substitution. Breitfussin A is of synthetic interest because of its novel structural features, as a final proof of its structure (since it was determined using nonstandard techniques) and to provide material for biological testing. In this thesis, efforts towards a synthesis of Breitfussin A are described as well as application of the synthetic strategy for making an analogue library. The synthesis features a Leimgruber-Batcho indole synthesis to prepare the correctly substituted indole. Two procedures were tested for introduction of the oxazole moiety: the Schöllkopf protocol and a Suzuki-Miyaura coupling. Development of iodination protocols are given much attention, and a novel regioselective oxazole iodination is presented. The synthesis of a late stage intermediate of Breitfussin A was performed in a shortest sequence of 11 steps from the commercially available starting material 2,6-DNP, in 12 % total yield. The whole strategy was successfully tested on a model compound with an unsubstituted indole, with the exception of the final deprotection. A range of compounds (at different stages in the synthesis) were produced for an analogue library.en_US
dc.identifier.urihttps://hdl.handle.net/10037/7680
dc.identifier.urnURN:NBN:no-uit_munin_7271
dc.language.isoengen_US
dc.publisherUiT Norges arktiske universiteten_US
dc.publisherUiT The Arctic University of Norwayen_US
dc.rights.accessRightsopenAccess
dc.rights.holderCopyright 2014 The Author(s)
dc.rights.urihttps://creativecommons.org/licenses/by-nc-sa/3.0en_US
dc.rightsAttribution-NonCommercial-ShareAlike 3.0 Unported (CC BY-NC-SA 3.0)en_US
dc.subject.courseIDKJE-3900en_US
dc.subjectVDP::Matematikk og Naturvitenskap: 400::Kjemi: 440::Organisk kjemi: 441en_US
dc.subjectVDP::Mathematics and natural science: 400::Chemistry: 440::Organic chemistry: 441en_US
dc.titleOn the Synthesis of Breitfussins. Toward the total synthesis of Breitfussin A and analoguesen_US
dc.typeMaster thesisen_US
dc.typeMastergradsoppgaveen_US


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Attribution-NonCommercial-ShareAlike 3.0 Unported (CC BY-NC-SA 3.0)
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