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

Gümüş A., MERT K.

HETEROCYCLIC COMMUNICATIONS, vol.21, no.1, pp.43-46, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 21 Issue: 1
  • Publication Date: 2015
  • Doi Number: 10.1515/hc-2014-0155
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.43-46
  • Van Yüzüncü Yıl University Affiliated: Yes


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.