Ashworth, Philip Anthony (1991) Synthetic approaches towards jaspamide. University of Southampton, Doctoral Thesis.
Abstract
The total synthesis of Jaspamide has been approached, using two novel organo-metallic reactions in the stereoselective formation of the trisubstituted double bond present in the polyketide portion of Jaspamide. The nickel(O) catalysed coupling of dihydropyrans with Grignard reagents, although unsuccessful, demonstrated many useful observations and provided a suitable conclusion to the previous work carried out in this field. The novel copper(I) catalysed coupling of organo-lithium reagents with dihydropyrans was utilised in the synthesis of the polyketide fragment, demonstrating a new synthetic method for the preparation of trisubstituted double bonds. A novel resolution of lactones and a new method for the preparation of metallated dihydropyrans has been demonstrated. Although Jaspamide itself was not completed, a macrocyclic derivative was produced demonstrating the methodology, which by modification will eventually lead to a total synthesis of Jaspamide.
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