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Synthesis of spirocyclic compounds containing quaternary carbon centres
Výbošťoková, Júlia ; Matoušová, Eliška (advisor) ; Baszczyňski, Ondřej (referee)
The main focus of this bachelor thesis is the preparation of spirocyclic compounds containing quaternary carbon centres. The key steps of the synthesis were palladium catalysed tandem cyclisation/Suzuki cross-coupling and subsequent halocarbocyclisation. The next step was oxidative opening of the tetrahydrofuran ring and following derivatisation of the resulting spirocyclic products. The prepared spirocyclic compounds will be tested for their possible cytotoxic effects. The first part of this work describes the preparation of starting materials which were subsequently subjected to the tandem cyclisation/Suzuki cross-coupling and halocarbocyclisation to form a quaternary carbon centre. In the second part, various oxidative conditions for tetrahydrofuran ring opening to form spirocyclic compounds are discussed. The last part of this work deals with the derivatisation of the synthesised spirocycles. Keywords: synthesis, spirocyclic compounds, quaternary carbon centres, cytotoxicity
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Synthesis of analogues of natural alkaloids containing quaternary carbon centres
Sádková, Michaela ; Matoušová, Eliška (advisor) ; Baszczyňski, Ondřej (referee)
This bachelor thesis is concerned with organic synthesis of polycyclic compounds containing quarternary carbon centres, which are structurally similar to Amaryllidaceae and Sceletium alkaloids. The aim of this work was to prepare compounds suitable for biological activity screening. To obtain the quarternary carbon centre, two key steps were used - tandem cyclisation/Suzuki cross-coupling and halocarbocyclisation. The first part of this work is focused on the synthesis of starting materials with two types of silyl groups. The second part deals with the preparation of quarternary carbon centre using tandem cyclisation/Suzuki cross-coupling and halocarbocyclisation. In the last part, experiments to form a double bond are described, together with its derivatisation to synthesise compounds with a potential biological activity. Key words: synthesis, alkaloids, Amaryllidaceae, Sceletium, polycyclic compounds, quarternary carbon centres
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Use of alkenylboronic acids in the tandem cyclisation/Suzuki cross-coupling
Klanicová, Kristýna ; Matoušová, Eliška (advisor) ; Míšek, Jiří (referee)
This thesis deals with the synthesis of polycyclic compounds using tandem cyclisation/Suzuki cross-coupling, by modification of the method developed by our research group. This thesis mainly investigates the scope of the tandem reaction with aliphatic boronic acids or their esters. The products of the palladium catalyzed reaction then underwent electrocyclization to form an aromatic ring. The polycyclic skeleton, containing the aromatic core, is found in a considerable amount of natural substances with biological activity. The structure of the compounds prepared herein is similar to miltiorin D or commiphorane A.
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