Synthesis of (+/-)-eusynstyelamide A

Org Lett. 2010 Jun 4;12(11):2664-7. doi: 10.1021/ol100896n.

Abstract

The synthesis of (+/-)-eusynstyelamide A has been accomplished in six steps in 13% overall yield from 6-bromoindole, methyl glycidate, and Boc-protected agmatine. If oxygen is carefully excluded from the reaction, the key NaOH-catalyzed aldol dimerization of the alpha-ketoamide proceeded efficiently to give Boc-protected eusynstyelamide A.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Catalysis
  • Hydrocarbons, Brominated / chemical synthesis*
  • Hydrocarbons, Brominated / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Hydrocarbons, Brominated
  • Indoles
  • eusynstyelamide A