Synthetic and Biophysical Studies on the Tridachiahydropyrone Family of Natural Products

This thesis addresses fundamental scientific questions such as:
How are complex natural products synthesized in vivo?
Can we replicate these conditions in a laboratory environment?
What is the biological function of such secondary metabolites?
What are the biological origins of chirality?
These issues are explored in an accessible manner using a multidisciplinary approach spanning chemistry, biology and physics to investigate an interesting family of complex natural products isolated from marine molluscs the tridachiahydropyrones.

The work has achieved:
Elegant biomimetic syntheses of a number of the tridachiahydropyrone compounds in vitro using organic synthesis techniques
The characterization of the interactions between these compounds and a range of model membrane systems using a series of fluorescence spectroscopic studies
The investigation of the antioxidant and photoprotective properties of the compounds by means of biophysical assay techniques
The synthesis of tridachiahydropyrone utilizing the model membrane systems as biomimetic reaction media.

Nominated as an outstanding Ph.D. thesis by the University of Nottingham, UK Includes a concise review of electrocyclizations in natural product synthesis Presents a multidisciplinary approach to the investigation of natural products spanning chemistry, biology, and physics Describes the total synthesis of a number of complex polypropionate natural products, as well as a new methodology for accessing alkenyl halides Includes supplementary material: sn.pub/extras

Klappentext
This thesis addresses fundamental scientific questions such as:
How are complex natural products synthesized in vivo?
Can we replicate these conditions in a laboratory environment?
What is the biological function of such secondary metabolites?
What are the biological origins of chirality?
These issues are explored in an accessible manner using a multidisciplinary approach spanning chemistry, biology and physics to investigate an interesting family of complex natural products isolated from marine molluscs the tridachiahydropyrones.

The work has achieved:
Elegant biomimetic syntheses of a number of the tridachiahydropyrone compounds in vitro using organic synthesis techniques
The characterization of the interactions between these compounds and a range of model membrane systems using a series of fluorescence spectroscopic studies
The investigation of the antioxidant and photoprotective properties of the compounds by means of biophysical assay techniques
The synthesis of tridachiahydropyrone utilizing the model membrane systems as biomimetic reaction media.

Inhalt
Introduction.- Synthesis of the Tridachiahydropyrones and their Biomimetic Precursors.- Interactions of the Tridachiahydropyrones with Model Membrane Systems: Biophysical Studies.- Investigations into the Photoprotective and Antioxidant Properties of the Tridachiahydropyrones.- Summary and Conclusions.- Experimental.- Synthesis of Alkenyl Nitriles by the Palladium-Catalysed Cyanation of Vinyl Halides with Acetone Cyanohydrin.