Stereocontrolled Synthesis and Structural Revision of Plebeianiol A
Lucas K. Johnson, Scott W. Niman, Darius Vrubliauskas, Christopher D. Vanderwal
Abstract
We report the structural revision via synthesis of the abietane diterpenoid plebeianiol A. The synthesis was accomplished by a short and convergent sequence that featured our previously established cobalt-catalyzed hydrogen-atom-transfer-induced radical bicyclization. We further connected plebeianiol A as the likely biogenetic precursor to another previously reported ether-bridged abietane. Finally, we demonstrated that the key cyclization event is efficient with the A-ring diol protected as two different cyclic acetals or in unprotected form.
Topics & Concepts
AbietaneChemistryDiolStereochemistrySequence (biology)Ring (chemistry)TemplateEtherHydrogen atomCombinatorial chemistryTerpenoidOrganic chemistryNanotechnologyGroup (periodic table)BiochemistryMaterials scienceBiological Activity of Diterpenoids and BiflavonoidsPlant biochemistry and biosynthesisPlant-based Medicinal Research