Approaches to the total synthesis of a novel diarylheptanoid

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Show simple item record Vela, Nomandla Magnificent 2010-08-18T08:49:13Z 2010-08-18T08:49:13Z 2008
dc.description Thesis (Ph.D. (School of Chemistry)) - University of KwaZulu-Natal, Pietermaritzburg, 2008. en_US
dc.description.abstract The total synthesis of a novel diarylheptanoid isolated from a South African medicinal plant, Siphonochilus aethiopicus, was investigated. S. aethiopicus (Indungulu in Zulu) is the only South African species of the Zingiberaceae plant family and is widely used in traditional medicine. One of the compounds isolated from this plant is a novel diarylheptanoid. Diarylheptanoids constitute a distinct group of natural plant metabolites characterized by two aromatic rings linked by a linear seven-carbon aliphatic chain, with varying functional groups on the aryl and the aliphatic chain. The target molecule for our synthesis contains two highly oxygenated aryl rings linked by an aliphatic chain with two stereogenic centres and a trans-alkene. In this study we present our investigation of different strategies to a viable synthetic method that could provide material to supplement the relatively small quantity of product that can be isolated from the plant extract. The major challenges of this synthesis were to develop procedures for the preparation of the homobenzylic trans-alkene, the stereogenic centres and to attach the electron-rich aromatic rings to the aliphatic chain. In this thesis the following aspects are described: • Various types of olefination reactions (including Wittig, Julia and organometalic-mediated type of olefination reactions) • Various types of alkylation reactions (including Grignard, Friedel-Crafts and organometalic-mediated type of alkylation reactions) • Incorporation of the stereogenic centres (including asymmetric hydroxylation and use of chiral starting materials) The synthesis will not only give a viable synthetic route to the target compound but is also versatile enough to allow the preparation of analogues. en_US
dc.language.iso en en_US
dc.subject Medicinal plants. en_US
dc.subject Metabolites. en_US
dc.subject Organic compounds--Synthesis. en_US
dc.subject Botany, Medical. en_US
dc.subject Siphonochilus aelthiopicus. en_US
dc.subject Theses--Chemistry. en_US
dc.title Approaches to the total synthesis of a novel diarylheptanoid en_US
dc.type Thesis en_US

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