Synthesis and biological evaluation of optically active conjugated gamma- and delta-lactone derivatives

ŞARDAN M., Sezer S., GUNEL A., AKKAYA M., TANYELİ C.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol.22, no.18, pp.5814-5818, 2012 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 22 Issue: 18
  • Publication Date: 2012
  • Doi Number: 10.1016/j.bmcl.2012.07.090
  • Journal Name: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5814-5818
  • Keywords: Asymmetric synthesis, Enzymatic resolution, Optically active lactones, RING-CLOSING METATHESIS, PYRUVATE-KINASE DEFICIENCY, ASYMMETRIC-SYNTHESIS, ANTIOXIDANT
  • Middle East Technical University Affiliated: Yes

Abstract

An efficient synthesis of racemic and both enantiomeric forms of heteroaryl substituted gamma- and delta-lactone derivatives derived from allyl and homoallyl alcohol backbones has been accomplished via ring closing metathesis reaction. 2-Heteroaryl substituted allyl and homoallyl alcohols have been efficiently resolved through enzymatic method with high ee (97-99%) and known stereochemistry. Antimicrobial and antioxidant activities of target lactones were evaluated. (C) 2012 Elsevier Ltd. All rights reserved.