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Studies directed towards the natural product nominine

Studies directed towards the natural product nominine
Studies directed towards the natural product nominine
Natural product synthesis is a highly regarded and essential aspect of organic chemistry. Its challenging nature requires a wide spectrum of reactions to be performed with a broad set of skills being developed throughout each project. This thesis describes studies towards the total synthesis of nominine, an indole diterpenoid which exhibits antiinsectant properties. Synthesis of this natural product could provide entry into this family of indole diterpenoids allowing several natural products to be accessed.

Chapter 1 introduces this natural product and its proposed synthetic route. Two total syntheses, by Bonjoch and Nicolaou published after this project had ceased, are also presented.

Chapter 2 discusses the methods of constructing key intermediate enone 1.1 and describes its successful efficient synthesis on a multigram scale. The synthesis of natural products dehydrofukinone and fukinone using this key intermediate follows in chapter 3.

Chapter 4 details the challenges and successes of the investigations towards the total synthesis of nominine. Future work for its completion and other possible related indole diterpenoids are described in chapter 5. A conclusion to the project and a chapter containing experimental details conclude this thesis.
Goh, Wendy
c98f778e-4b91-4962-a491-184b7c15e852
Goh, Wendy
c98f778e-4b91-4962-a491-184b7c15e852
Ganesan, Arasu
b089a6eb-86e6-4f65-878d-4766dfdeb6b7

(2013) Studies directed towards the natural product nominine. University of Southampton, Department of Chemistry, Doctoral Thesis, 187pp.

Record type: Thesis (Doctoral)

Abstract

Natural product synthesis is a highly regarded and essential aspect of organic chemistry. Its challenging nature requires a wide spectrum of reactions to be performed with a broad set of skills being developed throughout each project. This thesis describes studies towards the total synthesis of nominine, an indole diterpenoid which exhibits antiinsectant properties. Synthesis of this natural product could provide entry into this family of indole diterpenoids allowing several natural products to be accessed.

Chapter 1 introduces this natural product and its proposed synthetic route. Two total syntheses, by Bonjoch and Nicolaou published after this project had ceased, are also presented.

Chapter 2 discusses the methods of constructing key intermediate enone 1.1 and describes its successful efficient synthesis on a multigram scale. The synthesis of natural products dehydrofukinone and fukinone using this key intermediate follows in chapter 3.

Chapter 4 details the challenges and successes of the investigations towards the total synthesis of nominine. Future work for its completion and other possible related indole diterpenoids are described in chapter 5. A conclusion to the project and a chapter containing experimental details conclude this thesis.

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Published date: April 2013
Organisations: University of Southampton, Chemistry

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Local EPrints ID: 359288
URI: http://eprints.soton.ac.uk/id/eprint/359288
PURE UUID: 82e4001e-3bb2-4d61-b41f-6da1f5a56aa0

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Date deposited: 23 Dec 2013 12:14
Last modified: 18 Jul 2017 03:22

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