Abstract
Total synthesis of two arabidopyrones, iso-arabidopyl alcohol (1) and iso-arabidopic acid (2) isolated from Arabidopsis thaliana was achieved for the first time using Claisen condensation and Wittig reaction as the key steps. In addition, arabidopic acid (4) was synthesized from the methyl ester of arabidopyl alcohol (3). Thus, chemical synthesis of the unique natural α-pyrones 1–4 was accomplished with a short synthetic route by a systematic approach from readily available substances.
Graphical Abstract
Acknowledgement
We thank Dr. Clint Chapple (Purdue University) for invaluable discussions and providing NMR data of arabidopyrones. Dr. Yoichi Yamada (Utsunomiya University) for technical assistances of NMR and IR analyses.