Total Syntheses of Phleghenrines A and C
Xinpei Cai, Lei Li, Yecheng Wang, Jianhan Zhou, Mingji Dai
Abstract
High Resolution Image Download MS PowerPoint Slide Herein, we report the total syntheses of phleghenrines A and C from commercially available starting materials in 7 and 8 steps, respectively. Notable steps include an inverse electron-demand Diels–Alder reaction between a masked o -benzoquinone and a N -protected enamine to prepare one key intermediate with a bicyclo[2.2.2]octenone core, a Büchner–Curtius–Schlotterbeck one-carbon insertion to expand the bicyclo[2.2.2]octenone to a bicyclo[3.2.2]nonenone, and Trauner’s modified 2-pyridone synthesis to install the 2-pyridone moiety.
Topics & Concepts
ChemistryBicyclic moleculeMoietyEnamineTotal synthesisCurtius rearrangementStereochemistryCombinatorial chemistryOrganic chemistryCatalysisTraditional and Medicinal Uses of AnnonaceaeChemical synthesis and alkaloidsAsymmetric Synthesis and Catalysis