A Concise Enantioselective Approach to Quassinoids
William P. Thomas, Sergey V. Pronin
Abstract
A synthetic approach to quassinoids is described. The route to the tetracyclic core relies on an efficient and selective annulation between two unsaturated carbonyl components that is initiated by catalytic hydrogen atom transfer from an iron hydride to an alkene. Application of this strategy allows for enantioselective synthesis of quassin, which is prepared in 14 steps from commercially available starting material.
Topics & Concepts
ChemistryEnantioselective synthesisAnnulationAlkeneHydrideCatalysisCombinatorial chemistryStereochemistryOrganic chemistryHydrogenPhytochemical compounds biological activitiesCatalytic Alkyne ReactionsMulticomponent Synthesis of Heterocycles