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- W1933453119 abstract "The work presented in this thesis mainly describes the discovery and development ofmethodology for the synthesis of anthecularin and anthecotulides, a family of unusualsesquiterpene lactones.Firstly, two 1,3-dipolar cycloaddition approaches toward anthecularin have been evaluated, using either oxidopyrylium ylide chemistry (Path A) or carbonyl ylides, generated by rhodium-catalysed decomposition of diazo ketones (Path B). Synthesis of the key precursor for the diazo strategy was achieved but unfortunately no desired cycloadduct was isolated.Secondly, an experimentally straightforward method to stereoselectively synthesise β-hydroxymethyl-α-methylene-γ-butyrolactones was developed using chromium or zinc. The synthetic utility of this methodology was demonstrated in syntheses of (±)-methylenolactocin, (±)-hydroxymatairesinol and, ultimately, (±)-hydroxyanthecotulide using a gold-catalysed Meyer-Schuster rearrangement.Finally, the first asymmetric synthesis of (+)-anthecotulide has been achieved, in 6 steps from commercially available materials. During this synthesis the absolute configuration was established. Furthermore, a novel rhodium-catalysed enantioselective ene-yne cycloisomerisation was used to form the α-methylene-γ-butyrolactone core." @default.
- W1933453119 created "2016-06-24" @default.
- W1933453119 creator A5050035899 @default.
- W1933453119 date "2011-01-01" @default.
- W1933453119 modified "2023-09-27" @default.
- W1933453119 title "Towards the synthesis of anthecularin and anthecotulides" @default.
- W1933453119 hasPublicationYear "2011" @default.
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