Synthesis and biological evaluation of a potent salicylihalamide A lactam analogue.

@article{Balan2012SynthesisAB,
  title={Synthesis and biological evaluation of a potent salicylihalamide A lactam analogue.},
  author={Dan A Balan and Christopher John Burns and Nicholas G Fisk and Helmut M. Huegel and David S Huang and David Leslie Segal and Charlotte White and J{\"o}rg Wagler and Mark A Rizzacasa},
  journal={Organic & biomolecular chemistry},
  year={2012},
  volume={10 40},
  pages={
          8147-53
        }
}
The first synthesis of a lactam analogue of salicylihalamide A (1) is reported. A key step in the approach was a photochemical acylation coupling between amine 10 and dioxinone 9 to form the amide 19. Acetylation followed by RCM with Grubbs 1st generation catalyst gave the desired E-lactam 23 (E : Z ratio 87 : 13) as the major compound. Conversion of macrolactam 23 into the vinyl iodide 26 followed by Cu catalysed cross coupling with the diene amide 7 gave aza-salicylihalamide analogue 3 in… CONTINUE READING