The best of both worlds: The configurational assignment of a natural product—chivosazole A (1) isolated from myxobacteria—has been achieved for the first time through the combination of structure elucidation and genetic analysis. This was achieved by chemical degradation, analysis of the NMR data in combination with computer‐aided conformation analysis, and assignment of the amino acid sequence.
Gold and rings: The gold(I)-catalyzed addition of aldehydes to 1,6-enynes gives 1,3-dienes, by a cycloaddition/fragmentation process. 1,5-Enynes react with aldehydes and ketones by the 5-endo-dig pathway to give the corresponding cycloadducts.
The first synthesis of the highly biologically active chivosazole F is described. It features an intramolecular Stille coupling for the macrolactone formation and thereby circumvents the problem of isomerization associated with the tetraene segment. Additionally, the synthesis confirms the structure which has been proposed based solely on a combination of NMR/computational methods and genetic analysis.
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