An Efficient and Short Total Synthesis of (−)-Heliannuol A by Intramolecular Ullmann C−O Coupling for the Construction of an Eight-Membered Ether Ring

Tetsu Tsubogo, Fumiya Okamura, Akiho Omori, Hiromi Uchiro

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Herein, we report a method for the synthesis of eight-membered cyclic ethers by a direct C−O bond connection using an intramolecular Ullmann coupling reaction based on our previously published methodology. We found that allelopathically active heliannuol A could be rapidly synthesised using this method. The use of a strongly coordinating 4-pyrrolidinopyridine ligand accelerates the reaction rate and leads to the C−O coupling reaction of a typically inaccessible sterically bulky tertiary alcohol. Furthermore, this method circumvents the protection and deprotection steps, presenting a new strategy for the syntheses of benzannulated eight-membered ring structures.

Original languageEnglish
Pages (from-to)4224-4228
Number of pages5
JournalChemistrySelect
Volume6
Issue number17
DOIs
Publication statusPublished - 7 May 2021

Keywords

  • cyclization
  • eight-membered cyclic ether
  • Heliannuol A
  • total synthesis
  • Ullmann coupling

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