Efficient synthesis of karrikinolide via Cu(II)-catalyzed lactonization

Kazumasa Matsuo, Mitsuru Shindo

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

The efficient total synthesis of karrikinolide (KAR1), a potent plant growth regulator discovered in smoke from burning plant material, is described. 3-Hydroxy-4-pyranone, prepared from d-xylose, was subjected to a Cu(II)-catalyzed transesterification-Wittig lactonization to afford the dihydrofuropyran in good yield. Finally, radical bromination, followed by olefin formation, provided KAR1 in acceptable yield.

Original languageEnglish
Pages (from-to)971-975
Number of pages5
JournalTetrahedron
Volume67
Issue number5
DOIs
Publication statusPublished - Feb 4 2011

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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