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Title: π-allyltricarbonyliron lactone complexes : versatile tools for asymmetric synthesis
Author: Harter, Jürgen
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2002
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The opening chapter will give an introductory review of the chemistry of p-allyltricarbonyliron lactone complexes, in which their preparation and behaviour towards a variety of reagents is described. The utility of those complexes in organic synthesis to date will be outlined, with particular focus on controlling the stereochemical outcome of reactions carried out on functional groups appended to the organic ligand. In a further chapter, a synthetic route towards the total synthesis of the neutral product decarestrictine D will be described. Model studies will highlight the potential feasibility of employing the iron template in a route towards this target. In the following chapter, the synthesis of novel complexes with the side-chain attached to the C-2 position on the core allyl system will be discussed. Conformational analysis of these complexes employing modern NMR techniques will be outlined and studies on some addition attempt and the synthetic utility of these new compounds will be disclosed. Another chapter will describe the synthesis of chiral iron enoate ester complexes. Furthermore, the outcome of a variety of additions and cycloadditions into this new enoate ester functionality will be discussed. In a further chapter, the formal total synthesis of the natural product (-)-gloeosporone will be described. This route employs a 1,7 Mukaiyama aldol addition on a suitable iron lactone complex, a stereoselective reduction in the appended side-chain and a novel decomplexation step with lithium naphthalenide.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available