Title:
|
The total synthesis of lodopyridone
|
Natural products are an important and diverse class of compounds;
pyrones and pyridones, examples of their chemistry and natural products
featuring these structures are discussed. Lodopyridone (75) is introduced
as both a highly unusual natural product and a potential NQ02 inhibitor.
A number of simple lodopyridone inspired analogues were prepared as
potential NQ02 inhibitors and tested for binding to the enzyme. Synthetic
studies toward lodopyridone featuring acetylation, rearrangement and
cross coupling approaches to the key C-6 C-C bond formation were
explored. Pyrone 175 was prepared by Suzuki coupling and oxidation
studies towards amide 189, featuring a key modified Corey-Ganem-Gilman
reaction were explored. The key pryone 189 was converted to the
pyridone 196 and manipulation to complete the synthesis of lodopyridone
(75) was achieved.
Studies towards the related pyridone containing natural product antibiotic
B 90063 were performed and a synthetic strategy presented. Conclusion in
Chapter 3 and future work in Chapter 4 is presented followed by full
experimental procedures in Chapter 5.
|