Thesis

Towards the total synthesis of Agariblazeispirol C

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Awarding institution
  • University of Strathclyde
Date of award
  • 2011
Thesis identifier
  • T12724
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Abstract
  • The research described herein concerns the efforts towards the synthesis of the natural target Agariblazeispirol C, 1. Within the Kerr laboratory, a synthetic route towards this novel steroid had been proposed. At the outset, work focused on this initially envisaged preparative pathway, however, in due course, an additional and more convergent route was devised. Both proposed pathways for gaining access to Agariblazeispirol C centre on the strategic employment of metal-mediated cyclisation chemistry, specifically, a novel intramolecular Heck reaction and an intramolecular Pauson-Khand cyclisation. With regards to the construction of the main core of the molecule, the synthesis of a late stage intermediate has been accomplished. Various new strategies towards the completion of the synthesis have been devised and work has been initiated to execute these tactics. In addition to this, a series of optimisation studies on many of the individual steps have led to enhancements with respect to the overall efficiency of the route towards the natural product target. In addition to the above, X-ray crystallography was used to unambiguously determine the relative stereochemistry of a key tetracyclic synthetic intermediate.
Resource Type
DOI
Date Created
  • 2011
Former identifier
  • 820643

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