Synthesis and Utilization of Novel Chromone Based Scaffolds
Clark, Mitchell Robert
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Cite this item:
Clark, M. R. (2018). Synthesis and Utilization of Novel Chromone Based Scaffolds (Thesis, Master of Science). University of Otago. Retrieved from http://hdl.handle.net/10523/7933
Permanent link to OUR Archive version:
http://hdl.handle.net/10523/7933
Abstract:
The chromone moiety (11) is a common structural motif found in a wealth of natural products and medicinally relevant compounds. Its synthesis has been investigated for over 100 years, yet opportunities still remain for the development of synthetic methods which provide a broader substrate scope and increased efficiency.
The synthesis of 3 from 4 was discovered by members of our group, which provided a novel way of accessing the chromone scaffold. This new method showed promising signs of overcoming problems encountered in established synthetic methodology and provided chromones in moderate to good yields (30 – 60%). Additionally, this method provides functional handles, not accessible by established methodology, which we envisioned could be used to provide access to further elaborated natural product-like scaffolds.
This project investigated the scope of this reaction by varying portions of the molecule. The synthetic utility of the reaction was then explored by attempting a number of modifications to the relevant chromones, most notably the divinyl cyclopropane rearrangements to access chromone fused cycloheptadienes (76).
Date:
2018
Advisor:
Hawkins, Bill
Degree Name:
Master of Science
Degree Discipline:
Chemistry
Publisher:
University of Otago
Keywords:
Organic Synthesis; Chromone; natural products
Research Type:
Thesis
Languages:
English
Collections
- Chemistry [203]
- Thesis - Masters [4213]