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Synthesis of Highly Functionalised Furo[3,4-b]pyrans: Towards the Fungal Metabolite (−)-TAN-2483B

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dc.contributor.advisor Harvey, Joanne E.
dc.contributor.advisor Teesdale-Spittle, Paul
dc.contributor.author Somarathne, R.M. Kalpani K.
dc.date.accessioned 2014-11-23T23:32:16Z
dc.date.accessioned 2022-11-03T02:16:52Z
dc.date.available 2014-11-23T23:32:16Z
dc.date.available 2022-11-03T02:16:52Z
dc.date.copyright 2014
dc.date.issued 2014
dc.identifier.uri https://ir.wgtn.ac.nz/handle/123456789/29614
dc.description.abstract Carbohydrate-derived cyclopropanes combine both the stereochemical wealth of carbohydrates and the reactivity of cyclopropanes. A diverse variety of reaction modes for these cyclopropyl carbohydrates can be harnessed for the synthesis of natural products and other targets. The natural products (−)-TAN-2483A and (−)-TAN-2483B are fungal secondary metabolites displaying a variety of bioactivities such as inhibition of c-src kinase action and parathyroid hormone-induced bone resorption. This thesis described several synthetic approaches to the natural product (−)-TAN-2483B and analogues of (−)-TAN-2483B employing cyclopropane ring expansion. The synthetic route to (−)-TAN-2483B began with the readily available substrate D-mannose. The pyran ring unsaturation of the natural product was established by a cyclopropanation-ring expansion sequence. A synthetic strategy via dichlorocyclopropane-based intermediates is described in chapter 2. This being unsuccessful, an alternative approach via 2-fomyl-glycal was developed in chapter 3. The chapter 2 and 3 provided a solid background for the achievement of the analogues synthesis illustrated in chapter 4 via dibromocyclopropane. Lewis acid-mediated alkynylation followed by Pdcatalysed carbonylative lactonisation was successfully utilised in the revelation of the furo[3,4-b]pyran ring skeleton. This route afforded analogues of TAN-2483B; the Z-and E-unsaturated ethyl esters 140 and 141 and hydroxy(−)-TAN-2483B 145. The total synthesis of (−)-TAN-2483B was not achieved due to unforeseen obstacles encountered in the deoxygenation of the side arm of 335 (Chapter 4) into the E-propenyl side arm of (−)-TAN-2483B. en_NZ
dc.language.iso en_NZ
dc.publisher Te Herenga Waka—Victoria University of Wellington en_NZ
dc.rights Access is restricted to staff and students only until 12/2016. For information please contact the library. en_NZ
dc.subject TAN-2483B en_NZ
dc.subject Cyclopropane en_NZ
dc.subject Carbonylation en_NZ
dc.title Synthesis of Highly Functionalised Furo[3,4-b]pyrans: Towards the Fungal Metabolite (−)-TAN-2483B en_NZ
dc.type Text en_NZ
vuwschema.contributor.unit School of Chemical and Physical Sciences en_NZ
vuwschema.subject.anzsrcfor 030401 Biologically Active Molecules en_NZ
vuwschema.subject.anzsrcfor 030502 Natural Products Chemistry en_NZ
vuwschema.subject.anzsrcfor 030503 Organic Chemical Synthesis en_NZ
vuwschema.subject.anzsrcseo 970103 Expanding Knowledge in the Chemical Sciences en_NZ
vuwschema.type.vuw Awarded Doctoral Thesis en_NZ
thesis.degree.discipline Chemistry en_NZ
thesis.degree.grantor Te Herenga Waka—Victoria University of Wellington en_NZ
thesis.degree.level Doctoral en_NZ
thesis.degree.name Doctor of Philosophy en_NZ

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