|
|
Using tandem cyclisation/Sonogashira cross-coupling in the synthesis of natural products and their derivatives
Liška, Benno ; Matoušová, Eliška (advisor) ; Míšek, Jiří (referee)
The subject of this bachelor's thesis is the preparation of polycyclic compounds using the tandem cyclisation/Sonogashira cross-coupling and a potential application of this reaction to the synthesis of natural products and their derivatives. The aim was to study this method using nonaromatic starting materials with a six-membered ring and to explore possibilities for functionalisation of the triple bond of the newly prepared compounds. The first part of this thesis deals with the synthesis of starting materials containing either an ether group or a malonate residue. The second part deals with the optimisation of conditions and the investigation of the scope of Heck reaction and Sonogashira cross-coupling. The third part describes the attempts to hydrate the triple bond and the last part contains reactions with allylic alcohols. Keywords: synthesis, tandem reaction, natural products, Sonogashira cross-coupling, Heck reaction
|
|
|
Using Heck reaction for aromatic ring formation in the synthesis of polycyclic compounds
Bažíková, Ema ; Matoušová, Eliška (advisor) ; Míšek, Jiří (referee)
This bachelor's thesis focuses on the synthesis of a polycarbocyclic compound with naphthalene core and the following oxidation to the corresponding ortho-naphthoquinone. The naphthalene and naphthoquinone skeleton can be found in many natural products with interesting biological properties. This thesis extends the scope of a method developed by our group for the synthesis of naturally occurring ortho-naphthoquinones. The key step of the synthesis was to form an aromatic ring using the Heck reaction. Keywords: synthesis, polycyclic compounds, naphthalenes, catalysis, Heck reaction
|
|
|
Synthesis of all-carbon quaternary centres
Orlovská, Ľubica ; Matoušová, Eliška (advisor) ; Hájíček, Josef (referee)
In this diploma Thesis I dealt with the synthesis of nitrogen compounds that contain quaternary carbon centres and their structure resembles natural substances, specifically alkaloids from the Amaryllidaceae family. Halocarbocyclization or Heck reaction was planned as a key step of the synthesis, which should lead to the formation of quaternary carbon centres. First, starting nitriles and esters with five- and six-membered rings were prepared. Subsequently, the method for the preparation of a stable bicyclic ketone with a five-membered ring from an ester was optimized. The next part of the Thesis is devoted to the synthesis of a substrate for the Heck reaction from the prepared ketone, which was then used for the preparation of the alkaloid skeleton with a quaternary carbon centre, unfortunately without success so far. In the last part of the work, a bicyclic ketone with a six-membered ring, from which it is possible to prepare a substrate for the Heck reaction in several steps already used for five-membered substances, was prepared from the nitrile by carbopalladation. Key words: synthesis, quaternary carbon centres, Heck reaction, halocarbocyclisation, Amaryllidaceae alkaloids
|
guest ::
