Total Synthesis of (±)-Liphagal via Organic-Redox-Driven Palladium-Catalyzed Hydroxybenzofuran Formation

Eriko Tao, Masaki Inoue, Taejoo Jeong, In Su Kim, Takehiko Yoshimitsu

Research output: Contribution to journalArticlepeer-review

Abstract

A synthetic route to liphagal, a natural PI3Kα inhibitor isolated from Aka coralliphaga, was established. The present route features an organic redox process where an alkynylquinone undergoes reductive cyclization in the presence of a hydroquinone derivative such as hydroxyquinol (1,2,4-benzenetriol) and catalytic PdCl2 to provide a substituted benzofuran suitable for accessing the natural product. The benzofuran formation takes place via the redox transformation between the alkynylquinone and the electron-rich hydroquinones followed by the concomitant Pd(II)-catalyzed oxycyclization of the resultant alkynylhydroquinone.

Original languageEnglish
Pages (from-to)9064-9070
Number of pages7
JournalJournal of Organic Chemistry
Volume85
Issue number14
DOIs
Publication statusPublished - Jul 17 2020

ASJC Scopus subject areas

  • Organic Chemistry

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