Unified total synthesis of amorfrutins A and C via the Claisen rearrangement

Tadafumi Fujita, Shigefumi Kuwahara, Yusuke Ogura

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

A concise, unified total synthesis of the two prenylated aromatic polyketides amorfrutins A and C, which exhibit various medicinally important biological profiles such as antimicrobial, PPARã modulating and quorum sensing inhibitory activities, has been achieved from commercially available 3,5-dimethoxybenzaldehyde in 38% and 10% overall yields through nine and ten steps, respectively. The key transformation for the synthesis of amorfrutin A was the Claisen rearrangement of a mono-O-(1,1-dimethylallyl)resorcinol derivative to install the C3- prenyl substituent, while that for the synthesis of amorfrutin C was the double Claisen rearrangement of a di-O-(1,1-dimethylallyl)resorcinol derivative to introduce the two prenyl groups at the C3 and C5 positions all at once.

Original languageEnglish
Pages (from-to)1635-1641
Number of pages7
JournalBioscience, Biotechnology and Biochemistry
Volume83
Issue number9
DOIs
Publication statusPublished - 2019

Keywords

  • Amorfrutin
  • Amorpha fruticosa
  • Claisen rearrangement
  • Glycyrrhiza acanthocarpa
  • Total synthesis

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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