Chemoenzymatic synthesis of a 1,2,3-triazolo-delta-lactone derivative

Gümüş A., MERT K.

HETEROCYCLIC COMMUNICATIONS, cilt.21, sa.1, ss.43-46, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 21 Sayı: 1
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1515/hc-2014-0155
  • Dergi Adı: HETEROCYCLIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.43-46
  • Van Yüzüncü Yıl Üniversitesi Adresli: Evet

Özet

The stereoselective synthesis of a 1,2,3-triazolod-lactone (+)-6 derived from a homoallyl alcohol (S)-(-)-1 backbone was accomplished. 2-Thienyl-substituted allyl alcohol rac-1 was efficiently resolved through enzymatic method with high ee (95%) and known stereochemistry. An enantiomerically enriched azidoalcohol (+)-4 derived from a homoallyl alcohol was subjected to the Huisgen 1,3-dipolar cycloaddition reaction with diethyl acetylenedicarboxylate, followed by intramolecular cyclization of the corresponding cycloadduct (+)-5, to yield the 1,2,3-triazolo-delta-lactone derivative.