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

Student thesis: Doctoral Thesis

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.
Date of Award31 Oct 2019
Original languageEnglish
Awarding Institution
  • University Of Strathclyde
SponsorsEPSRC (Engineering and Physical Sciences Research Council)
SupervisorWilliam Kerr (Supervisor) & Craig Jamieson (Supervisor)

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