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Construction of Various Bridged Polycyclic Skeletons by Palladium‐Catalyzed Dearomatization

Xingye Mu, Hanxiao Yu, Henian Peng, Wenrui Xiong, Ting Wu, Wenjun Tang

2020Angewandte Chemie International Edition59 citationsDOI

Abstract

A powerful palladium-catalyzed dearomative cyclization was developed that provides facile access to eight types of bridged tetracyclic skeletons bearing various ring sizes and heterocycles. With this method, several skeletons or analogues of natural products, including tubingensin B and dracaenones, were synthesized. Asymmetric dearomative cyclization enables the construction of various enantiomerically enriched bridged polycyclic systems with up to 99 % ee by employing a chiral palladium catalyst.

Topics & Concepts

PalladiumCatalysisRing (chemistry)ChemistryCombinatorial chemistryOrganic chemistryStereochemistryChemical synthesis and alkaloidsMarine Sponges and Natural ProductsTraditional and Medicinal Uses of Annonaceae
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