A new glycociamidine ring precursor: syntheses of (Z)-hymenialdisine, (Z)-2-debromohymenialdisine, and (+/-)-endo-2-debromohymenialdisine

Org Lett. 2005 Dec 8;7(25):5641-4. doi: 10.1021/ol052266m.

Abstract

[chemical reaction: see text]. The synthesis of the C11H5 marine sponge alkaloids, (Z)-hymenialdisine and (Z)-2-debromohymenialdisine, is described. A key step was the condensation between aldisine or its monobromo derivative and a new, efficient imidazolinone-based glycociamidine precursor. In the first case, the main product turned out to be the unprecedented (+/-)-endo-2-debromohymenialdisine.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry*
  • Animals
  • Azepines / chemical synthesis*
  • Azepines / chemistry*
  • Cyclization
  • Marine Biology
  • Molecular Structure
  • Porifera / chemistry
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry*
  • Stereoisomerism

Substances

  • Alkaloids
  • Azepines
  • Pyrroles
  • debromohymenialdisine
  • hymenialdisine