Synthesis of a laterally branched polyamine from alpha-methylene-gamma-butyrolactone

Org Lett. 2005 Jun 23;7(13):2663-5. doi: 10.1021/ol050803x.

Abstract

[reaction: see text] A polyamine derivative was prepared from alpha-methylene-gamma-butyrolactone. This method used Michael addition and lactone aminolysis followed by the nucleophilic substitution of the hydroxyl group by an azido group. The coupling of a lipophilic alkyne led to a polyamine that will be probed as a gene transfer agent.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • Alkynes / chemistry*
  • Catalysis
  • Furans / chemistry*
  • Molecular Structure
  • Polyamines / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkynes
  • Furans
  • Polyamines
  • alpha-methylene gamma-butyrolactone
  • 4-Butyrolactone