Pd(II)-Catalyzed Synthesis of Bicyclo[3.2.1] Lactones Tandem Intramolecular β-C(sp)-H Olefination and Lactonization of Free Carboxylic Acids

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2022 Jun 28

PMID 35763801

Authors

Martin Tomanik

Shaoqun Qian

Jin-Quan Yu

Affiliations

Soon will be listed here.

Abstract

Bicyclo[3.2.1] lactones are chemical scaffolds found in numerous bioactive natural products. Herein, we detail the development of a novel palladium(II)-catalyzed tandem intramolecular β-C(sp)-H olefination and lactonization reaction that rapidly transforms linear carboxylic acid possessing a tethered olefin into the bicyclo[3.2.1] lactone motif. This transformation features a broad substrate scope, shows excellent functional group compatibility, and can be extended to the preparation of the related seven-membered bicyclo[4.2.1] lactones. Additionally, we demonstrate the synthetic potential of this annulation by constructing the 6,6,5-tricyclic lactone core structure of the meroterpenoid cochlactone A. We anticipate that this compelling reaction may provide a novel synthetic disconnection that can be broadly applied toward the preparation of a variety of bioactive natural products.

Citing Articles

Ligand-Enabled Double γ-C(sp )-H Functionalization of Aliphatic Acids: One-Step Synthesis of γ-Arylated γ-Lactones.

Hoque M, Yu J Angew Chem Int Ed Engl. 2023; 62(49):e202312331.

PMID: 37851865 PMC: 11221842. DOI: 10.1002/anie.202312331.

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