Thesis

Structural determination of highly flexible oxylipin natural products via computationally-guided synthesis

Creator
Rights statement
Awarding institution
  • University of Strathclyde
Date of award
  • 2020
Thesis identifier
  • T15462
Person Identifier (Local)
  • 201583953
Qualification Level
Qualification Name
Department, School or Faculty
Abstract
  • A programme of work to further our research towards the total synthesis of (-)-mucosin, a highly flexible oxylipin, has been carried out. This resulted in the investigation of multiple synthetic strategies to afford the desired natural product. These strategies all involved the use of the Kerr group's magnesium bisamide-mediated asymmetric deprotonation methodology as an efficient transformation to introduce asymmetry in our synthesis, and to facilitate the synthesis towards (-)-mucosin. Additionally, the group's magnesium carbon-centered base technology was employed in this work, to aid in delivering the natural product.Following publications from independent researchers, there was strongly compelling evidence suggesting (-)-mucosin had been incorrectly assigned. Considering this, computational chemistry was employed to allow us to propose a probable structure for (-)-mucosin by comparing calculated NMR spectral data with the experimental data available in the chemical literature. Multiple quantitative approaches towards assigning probabilities to possible candidate structure were assessed.
Advisor / supervisor
  • Kerr, William
Resource Type
DOI
Date Created
  • 2019
Former identifier
  • 9912787893102996
Embargo Note
  • This thesis is restricted to Strathclyde users only until 1st April 2025.

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