Total Synthesis of (+)-CIS- and (+)-Trans-Sativenediol

Abstract

Very recently, two research group independently reported the isolation and structural elucidation of a new tricyclic sesquiterpenoid diol, (-)-cis-sativenediol (1). This compound, obtained from the fungi Helminthosporium sativum and Cochliobolus setariae IF0 6635, is a plant growth promotor with gibberellin like activity. Co-occurring with 1 was an isomeric substance, also levorotatory, to which was initially assigned the trans-sativenediol structure 2. However, more recently, Dorn and Arigoni have convincingly shown that the second natural product actually possesses the isosativenediol structure 3. We report herein the total synthesis of both (+)-cis- and (+)-trans-sativenediol (4 and 5, respectively). Our work fully confirms the structural assignment made in the case of 1, and also clearly shows that the structural assignment originally made in the case of 2 was indeed incorrect.