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The key reactions in the general synthesis of strobilurins are the highly (Z)-selective Wittig reaction of an (E)-cinnamaldehyde with the phosphorus ylide 8 derived from (1,1-dibromoethyl)triphenylphosphonium bromide, followed by bromine-iodine exchange and Pd-Cu co-catalyzed Stille cross-coupling of the resulting alkenyl iodide with methyl (Z)-2-tributylstannyl-3-methoxyacrylate (7). The synthetic...
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 1 H NMR variant of Mosher's method. (S)-3 is identical with the compound derived from the natural products...
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