Biomimetic Synthesis of Azorellolide via Cyclopropylcarbinyl Cation Chemistry
Jordan Y. Artzy, Dean J. Tantillo, Dirk Trauner
Abstract
A concise synthesis of the complex diterpene azorellolide, inspired by speculations on biosynthetic cationic cascades, is presented. The approach, guided by computation, relies on the intramolecular interception of a cyclopropylcarbinyl cation by an appended carboxylate. The successful execution of this strategy was achieved through acid-catalyzed isomerization of a β-lactone in competition with a type I dyotropic rearrangement.
Topics & Concepts
ChemistryIsomerizationIntramolecular forceDiterpeneCationic polymerizationCombinatorial chemistryLactoneCarboxylateStereochemistryOrganic chemistryCatalysisSynthetic Organic Chemistry MethodsPlant biochemistry and biosynthesisMarine Sponges and Natural Products