Synthesis of Karrikinolide Using the Aldol-Type Acetal Addition Reaction

Kanade Kirita, Seijiro Hosokawa

Research output: Contribution to journalArticlepeer-review

Abstract

A short step total synthesis of karrikinolide has been achieved. Both α and α′ positions of O-acylated acetol were alkylated by the boron-mediated aldol-type acetal addition reaction. The one-pot sequence including the Arbuzov reaction, intramolecular Horner-Wadsworth-Emmons reaction, acidic hydrolysis of acetals, and pyran formation provided karrikinolide. This procedure was applicable to the gram-scale synthesis of karrikinolide.

Original languageEnglish
Pages (from-to)3936-3941
Number of pages6
JournalJournal of Organic Chemistry
Volume85
Issue number5
DOIs
Publication statusPublished - 2020 Mar 6

ASJC Scopus subject areas

  • Organic Chemistry

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