Pd(II)-Catalyzed Synthesis of Bicyclo[3.2.1] Lactones via Tandem Intramolecular β-C(sp3)-H Olefination and Lactonization of Free Carboxylic Acids

Martin Tomanik, Shaoqun Qian, Jin Quan Yu

Research output: Contribution to journalArticlepeer-review

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(sp3)-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.

Original languageEnglish (US)
Pages (from-to)11955-11960
Number of pages6
JournalJournal of the American Chemical Society
Volume144
Issue number27
DOIs
StatePublished - Jul 13 2022

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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