Cristin-resultat-ID: 1646773
Sist endret: 26. februar 2019, 14:57
Resultat
Doktorgradsavhandling
2018

Diels-Alder reactions in synthesis and method development

Bidragsytere:
  • Jakob Karl Kristoffer Wåhlander

Utgiver/serie

Utgiver

University of Oslo

Serie

Series of dissertations submitted to the Faculty of Mathematics and Natural Sciences, University of Oslo.
ISSN 1501-7710
NVI-nivå 0

Om resultatet

Doktorgradsavhandling
Publiseringsår: 2018
Hefte: 2018
Antall sider: 107

Klassifisering

Fagfelt (NPI)

Fagfelt: Kjemi og materialteknologi
- Fagområde: Realfag og teknologi

Beskrivelse Beskrivelse

Tittel

Diels-Alder reactions in synthesis and method development

Sammendrag

This thesis has got two parts within the common theme of Diels-Alder reactions. One part starts with the group of natural products called asmarines. These compounds, which were found in the red sea sponges, were believed to have anti-cancer properties. However a synthetic pathway to these compounds does as of yet not exist. A potential synthetic pathway for a fragment of the asmarines was devised, using a Diels-Alder reaction in a crucial step. The other part starts with thioureas, a class of compounds that act as Diels-Alder catalysts by way of hydrogen bond activation of and α,β-unsaturated carbonyl compound. A new, but similar, phosphordiamide based framework that was hypothesized to act in a similar manner to the thioureas. It was thought that a functioning phosphordiamide catalyst could be used in the crucial Diels-Alder reaction of the asmarine fragment. A more in detail description is found in Chapter 1. In Chapter 2 the initial attempts at producing a functional phosphordiamide catalyst are presented. A few simple catalysts are produced and evaluated using several different systems. The compounds are however unsuccessful as Diels-Alder catalysts. Further studies of phosphordiamides can be found in Chapter 3 which deals with a computational study a new set of phosphordiamide catalysts, with more successful results. The Chapter 4 deals with the previously discussed synthetic pathway of an asmarine fragment. The idea of using a phosphordiamide as a catalyst was discarded in favor of a Lewis acid catalyst. Though the synthesis of the fragment was not complete, the main Diels-Alder step was eventually overcome and several more steps were completed with good yields. The final Chapter 5 describes a possible continuation to both projects.

Bidragsytere

Jakob Karl Kristoffer Wåhlander

  • Tilknyttet:
    Forfatter

Mohamed Amedjkouh

  • Tilknyttet:
    Veileder
    ved Katalyse ved Universitetet i Oslo

Lise-Lotte Gundersen

  • Tilknyttet:
    Veileder
    ved Organisk kjemi ved Universitetet i Oslo
1 - 3 av 3