A Catalytic Asymmetric Pictet–Spengler Platform as a Biomimetic Diversification Strategy toward Naturally Occurring Alkaloids
Manuel J. Scharf, Benjamin List
Abstract
-carbamoyl-β-arylethylamines with diverse aldehydes toward enantioenriched THIQs. The obtained products proved to be competent intermediates in the synthesis of THIQ, aporphine, tetrahydroberberine, morphinan, and androcymbine natural products. Novel catalyst design with regard to the stabilization of cationic intermediates was crucial to accomplish high reactivity while simultaneously achieving unprecedented stereoselectivity for the reaction of biologically relevant substrates.
Topics & Concepts
ChemistryDiversification (marketing strategy)Pictet–Spengler reactionCatalysisBiochemical engineeringOrganic chemistryBusinessMarketingEngineeringChemical synthesis and alkaloidsSynthesis and Biological ActivityBerberine and alkaloids research