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, cilt.22, sa.18, ss.5814-5818, 2012 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 22 Sayı: 18
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1016/j.bmcl.2012.07.090
  • Dergi Adı: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.5814-5818
  • Anahtar Kelimeler: Asymmetric synthesis, Enzymatic resolution, Optically active lactones, RING-CLOSING METATHESIS, PYRUVATE-KINASE DEFICIENCY, ASYMMETRIC-SYNTHESIS, ANTIOXIDANT
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.