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The synthesis of gem-difluoroshikimic acid derivatives
Başlık:
The synthesis of gem-difluoroshikimic acid derivatives
Yazar:
Humphreys, Jane, author.
ISBN:
9780438085282
Yazar Ek Girişi:
Fiziksel Tanımlama:
1 electronic resource (237 pages)
Genel Not:
Source: Dissertation Abstracts International, Volume: 76-08C.
Özet:
This thesis details the on-going work towards the synthesis of 6,6-difluoroshikimic acid, a fluorinated analogue of shikimic acid, targeted as a pro-drug for a possible anti-bacterial, anti-fungal, herbicidal and anti-parasitic agent. Chapter 1 briefly explores the development and mechanism of action of antibiotics and the growing threat of malaria. The shikimic acid pathway and, in particular, the action of the enzyme chorismate synthase is detailed. Known inhibitors of enzymes of the pathway, their syntheses and biological activity are discussed. The use of fluorine in bio-organic chemistry is summarised and several existing syntheses of fluorinated shikimic acid derivatives are outlined. To conclude, a previous approach towards 6,6-difluoroshikimic acid is described. Chapter 2 discusses a number of different synthetic approaches towards the target compound. The first route is a continuation of previous research conducted within the group utilising the enantiopure diol derived from bromobenzene dihydroxylation. Investigations have shown that a fluorodeoxygenation step gives improved yields of product if conducted at ultra-high pressure. Model studies into an allylic oxidation and suitable protecting group are discussed as part of this work. Subsequent routes utilising (-)-quinic acid as starting material are also detailed herein. The first of these alternate proposals involves the synthesis of a cross-conjugated enone that is easily fluorinated at atmospheric pressure. Attempts at a radical decarboxylation are discussed and two solutions to overcome some encountered problems are proposed. The first involves an oxidation at an allylic position; the second requires a reduction-oxidation- reduction sequence to avoid decarboxylation. In both cases, an allylic oxidation reaction is discussed. The fluorodeoxygenation reaction is explored in more detail, and the results lead to the final synthetic proposal which utilises the diol of the original route and involves a selective protection of one hydroxyl of a diol via a stannylene acetal. The synthesis of 3-deoxy-3,3-difluoroshikimic acid is discussed and compared to existing routes.
Notlar:
School code: 1543
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Yer Numarası | Demirbaş Numarası | Shelf Location | Lokasyon / Statüsü / İade Tarihi |
---|---|---|---|
XX(686946.1) | 686946-1001 | Proquest E-Tez Koleksiyonu | Arıyor... |
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