Synthetic study of yonarolide: stereoselective construction of the tricyclic core

• DOI: 10.1016/j.tetlet.2011.04.092
• Publication Date: 2011-05-07T20:32:48Z
• Authors: Yohei Ueda; Hideki Abe; Kazuo Iguchi; Hisanaka Ito
• Keywords: Epimer; Tricyclic; Aldol condensation; Michael reaction; Aldol reaction; Diels–Alder reaction

Stereoselective construction of the tricyclic core of yonarolide (1), a marine norditerpenoid, was achieved. This synthetic route includes a Diels–Alder reaction and an intramolecular aldol condensation. It also involves efficient epimerization through a retro-Michael reaction–Michael addition and will be applicable to the total synthesis of 1.