Adamantyl-β-butyrolactones: Synthesis and ring-opening reactions

Marija Matković, Krešimir Molčanov, Robert Glaser, Kata Mlinarić-Majerski

Research output: Contribution to journalArticlepeer-review

3 Scopus citations


2-(1-Adamantyl)-β-butyrolactones 3a and 3b were synthesized using very common peptide coupling reagents under mild conditions and their ring-opening reactions were then studied. These novel lactones showed pronounced stability and were resistant to cleavage upon acidic water extraction and column chromatographic purification. The adamantane moiety plays an important function in lowering the lactone reactivity by protecting the electrophilic sites on the four membered ring via steric hindrance. However under certain conditions, both O-C(carbonyl) and O-C(alkyl) bond-cleavage ring-opening reactions were observed. Bond-cleavage at physiological temperature makes these novel lactones especially noteworthy. Novel adamantyl-β-butyrolactones have a potential to act as biomembrane soluble amphiphiles that might exhibit a combination of stability and biological activity with the latter hopefully predominating.

Original languageEnglish
Pages (from-to)8795-8804
Number of pages10
Issue number42
StatePublished - 21 Oct 2012


  • Adamantyl-β-butyrolactones
  • C(alkyl)-O(acyl) bond-cleavage
  • C(carbonyl)-O(acyl) bond-cleavage
  • Lactonization
  • β-Lactones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


Dive into the research topics of 'Adamantyl-β-butyrolactones: Synthesis and ring-opening reactions'. Together they form a unique fingerprint.

Cite this