New benzodioxepin type strobilurins from basidiomycetes. Structural revision and determination of the absolute configuration of Strobilurin D (cas 132056-04-3) and related β-methoxyacrylate antibiotics

Add time:08/01/2019    Source:sciencedirect.com

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-field 1H NMR variant of Mosher's method. (S)-3 is identical with the compound derived from the natural products. In the course of these investigations the epoxide structures 15, 16 and 17 previously assigned to Strobilurin D (cas 132056-04-3), 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).

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