title: Ravynic acid, an antibiotic polyeneyne tetramic acid from Penicillium sp. elucidated through synthesis.
abstract: A new antibiotic natural product, ravynic acid, has been isolated from a Penicillium sp. of fungus, collected from Ravensbourne National Park. The 3-acylpolyenyne tetramic acid structure was definitively elucidated via synthesis. Highlights of the synthetic method include the heat induced formation of the 3-acylphosphorane tetramic acid and a selective Wittig cross-coupling to efficiently prepare the natural compounds carbon skeleton. The natural compound was shown to inhibit the growth of Staphylococcus aureus down to concentrations of 2.5 µg mL(-1).
authors: Research School of Chemistry, Australian National University, Canberra, ACT 2601, Australia. rab@anu.edu.au.
authors: J D
authors: JD
authors: Myrtle
authors: A M
authors: AM
authors: Beekman
authors: R A
authors: RA
authors: Barrow
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D010407:Penicillium / Q000737:chemistry*; D010753:Phosphoranes / Q000138:chemical synthesis; D020005:Propanols / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: D000480:Alkynes; D000900:Anti-Bacterial Agents; D010753:Phosphoranes; D020005:Propanols; D011760:Pyrrolidinones; C470524:ravenic acid; C009435:tetramic acid; C028255:propargyl alcohol