Cascade Claisen and Meinwald Rearrangement for One-Pot Divergent Synthesis of Benzofurans and 2<i>H</i>-Chromenes
Liyan Song, Su Qian, Xi Lin, Zhihui Du, Huiyou Xu, Ming‐An Ouyang, Hongliang Yao, Rongbiao Tong
Abstract
A new cascade approach has been developed for the one-pot four-step divergent synthesis of polysubstituted benzofurans and 2H-chromenes, featuring a novel cascade aromatic Claisen rearrangement/Meinwald rearrangement/dehydrative or oxidative cyclization. This new method was demonstrated with 39 examples tolerating different substitutions at an epoxide, allylic ether, and aromatic ring, and we showcased its utility with the first total synthesis of natural product liparacid A in seven steps.
Topics & Concepts
Claisen rearrangementChemistryAllylic rearrangementCascadeEpoxideCascade reactionNatural productCarroll rearrangementEtherRing (chemistry)StereochemistryCombinatorial chemistryTotal synthesisOrganic chemistryCatalysisChromatographyOxidative Organic Chemistry ReactionsSynthesis of Organic CompoundsMarine Sponges and Natural Products