Catalytic Enantioselective Total Synthesis of (+)–Lycoperdic Acid
Sami Kortet, Aurélie Claraz, Petri M. Pihko
Abstract
A concise enantio- and stereocontrolled synthesis of (+)-lycoperdic acid is presented. The stereochemical control is based on iminium-catalyzed Mukaiyama-Michael reaction and enamine-catalyzed organocatalytic α-chlorination steps. The amino group was introduced by azide displacement, affording the final stereochemistry of (+)-lycoperdic acid. Penultimate hydrogenation and hydrolysis afforded pure (+)-lycoperdic acid in seven steps from a known silyloxyfuran.
Topics & Concepts
ChemistryEnamineIminiumEnantioselective synthesisCatalysisAzideHydrolysisOrganic chemistryStereochemistryCombinatorial chemistryAsymmetric Synthesis and CatalysisMicrobial Natural Products and BiosynthesisTraditional and Medicinal Uses of Annonaceae