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Towards Total Synthesis of Steganone via Copper Mediated Atom Transfer Radical Cyclisation
[Thesis]. Manchester, UK: The University of Manchester; 2011.
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Abstract
Studies towards the total synthesis of steganone, a naturally occurring lignan lactone were attempted from a readily available starting material piperonal. The γ-lactone moiety present in steganone was synthesised using a copper mediated Atom Transfer Radical Cyclisation (ATRC) reaction. Introduction of the oxygen functionality has been achieved by a silver salt-mediated displacement reaction. The final steps involving the biaryl coupling still need further investigations.Two routes were initially chosen for the synthesis. The first used a piperonal substituent and the other used a bromopiperonal analogue. The piperonal route proved to be the more efficient.In previous studies, copper-mediated radical cyclisation reactions had been shown to be stereoselective. Based on the diastereoselective formations of γ-lactones, using the ATRC reaction, with a bromopiperonal substituent and a piperonal substituent, a plausible reason behind the stereoselective nature of this reaction has also been proposed.ATRC reactions on allylic monoiodoacetate analogues have also been attempted, with a view that it would give rise to a more reactive iodo functionality. Further studies on this substrate are still necessary, using various other radical initiators.