Stipitatic acid 12 is an aromatic seven-membered ring produced by Talaromyces stipitatus (previously known as Penicillium stipitatus). The identification of this secondary metabolite changed the concept of aromaticity and paved the way for the structural elucidation of many non-benzenoid aromatic natural products called tropolones. Stipitatic acid has undergone one of the most detailed isotopic labelling studies to understand how nature could form such an aromatic seven-membered ring under biological conditions. The incorporation of labelled acetate units into the carbon skeleton of stipitatic acid pointed to a polyketide origin for this fungal tropolonoid metabolite. Further labelling study using radioactive molecules of 3-methylocinaldehyde 29 suggested an oxidative ring expansion rearrangement for the formation of the tropolone seven-membered ring.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:633251 |
| Date | January 2014 |
| Creators | Fahad, Ahmed Al |
| Publisher | University of Bristol |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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