New benzodioxepin type strobilurins from basidiomycetes. Structural revision and determination of the absolute configuration of strobilurin D and related β-methoxyacrylate antibiotics

  • Hellwig V
  • Dasenbrock J
  • Klostermeyer D
 et al. 
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Abstract

The new antifungal strobilurins I (1) and K (19) are 3,4-dihydro-2H- benzo[b][1,4]dioxepin derivatives. Their structure and stereochemistry was determined by degradation to aldehyde 3. Both enantiomers of 3 were synthesised and the absolute configurations assigned by the high-field1H NMR variant of Mosher's method. (S)-3 is identical with the compound derived from the natural products. In the course of those investigations the epoxide structures 15, 16 and 17 previously assigned to strobilurin D, hydroxystrobilurin D and 9-methoxystrobilurin K have to be changed in 18, 21 and 20, respectively. All these compounds possess the same benzodioxepin core structure and (S)-configuration as strobilurin I (1).

Author-supplied keywords

  • Antifungals
  • Benzodioxepins
  • Natural Products
  • Regiochemistry
  • Strobilurins

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Authors

  • Veronika Hellwig

  • Johannes Dasenbrock

  • Dörte Klostermeyer

  • Stefan Kroiß

  • Tilman Sindlinger

  • Peter Spiteller

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