<scp>Palladium‐Catalzyed</scp> Atroposelective <scp>16‐Membered</scp> Macrocyclization: Total Synthesis of Isoplagiochin D<sup>†</sup>
Junwei Xi, Zhenhua Gu
Abstract
Summary of main observation and conclusion Isoplagiochin D is a ring‐strained macrocyclic bisbibenzylis, which showed stable axial chirality in one biaryl structure, and semistable axial chirality in the other biaryl moiety. We reported here an unprecedented example for the catalytically asymmetric synthesis of ring‐strained atropisomers via Pd‐catalyzed macrocyclization between benzyl halides and carbenes. This newly developed Pd‐catalyzed asymmetric macrocyclization protocol enabled us a quick synthesis of isoplagiochin D in a highly enantioselective manner.
Topics & Concepts
ChemistryAtropisomerMoietyAxial chiralityEnantioselective synthesisStereochemistryRing (chemistry)Chirality (physics)PalladiumTotal synthesisCombinatorial chemistryCatalysisOrganic chemistryQuarkChiral symmetry breakingPhysicsNambu–Jona-Lasinio modelQuantum mechanicsAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAlkaloids: synthesis and pharmacology