Total Synthesis of the Putative Structure of Asperipin-2a and Stereochemical Reassignment
Sadegh Shabani, Jonathan M. White, Craig A. Hutton
Abstract
The total synthesis of the putative structure of asperipin-2a is described. The synthesis features ether cross-links between the phenolic oxygen of Tyr6 and the β position of Tyr3 and the phenolic oxygen of Tyr3 and the β position of Hpp1 in the unique 17- and 14-membered bicyclic structure of asperipin-2a, respectively. The synthesized putative structure does not match the natural product, and a stereochemical reassignment is postulated.
Topics & Concepts
ChemistryNatural productStereochemistryTotal synthesisEtherBicyclic moleculeOxygenOrganic chemistryMicrobial Natural Products and BiosynthesisAdvanced Synthetic Organic ChemistryChemical synthesis and alkaloids