Development of asymmetric Tsuji-Trost allylation methodology: application towards the total synthesis of (+)-Zoapatanol

Skardon-Duncan, James (2019) Development of asymmetric Tsuji-Trost allylation methodology: application towards the total synthesis of (+)-Zoapatanol. PhD thesis, University of Glasgow.

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This thesis describes the application of the asymmetric Tsuji-Trost allylation reaction to the functionalisation of medium-sized cyclic ethers. The aims of the work described within this thesis were to develop and optimise methodology for the palladium-catalysed stereoselective allylation of cyclic ether systems and then showcase this methodology in the total synthesis of the bioactive diterpenoid natural product (+)-zoapatanol.

The first chapter provides a thorough literature review of the natural product (+)-zoapatanol, detailing its structure and origin, biological activity and previous efforts towards its synthesis. Following this, there is an extensive literature review of the key synthetic methodology utilised throughout this work, namely the Tsuji-Trost allylation reaction.

The second chapter documents the synthesis of four medium-sized cyclic ether substrates and the results obtained from the application of the Tsuji-Trost allylation reaction to the stereoselective functionalisation of these systems. It was discovered that the reaction could be tuned to deliver the desired stereoisomer and that both the ring size and substitution at the position of allylation impacted the inherent substrate selectivity. Subsequently, the results obtained during studies towards the total synthesis of (+)-zoapatanol are presented. A robust route to the core structure of zoapatanol was established and the asymmetric Tsuji-Trost methodology was successfully applied during this route.

The third chapter provides conclusions and potential future directions to build upon the work presented herein.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Zoapatanol, Tsuji-Trost allylation, asymmetric allylation, stereoselective allylation, cyclic ether, synthetic methodology, natural product, total synthesis.
Subjects: Q Science > QD Chemistry
Colleges/Schools: College of Science and Engineering > School of Chemistry
Supervisor's Name: Clark, Professor Stephen
Date of Award: 2019
Embargo Date: 13 February 2023
Depositing User: Mr James Skardon-Duncan
Unique ID: glathesis:2019-79020
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 13 Feb 2020 15:44
Last Modified: 28 Feb 2020 12:00
Thesis DOI: 10.5525/gla.thesis.79020
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