Synthesis of amorfrutins B and D from amorfrutin A ethyl ester

Tadafumi Fujita, Shigefumi Kuwahara, Yusuke Ogura

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Synthesis of the geranylated dihydrostilbenoid amorfrutin B with antimicrobial, PPARγ modulating and quorum sensing inhibitory activities has been achieved from amorfrutin A ethyl ester by a seven-step sequence involving the Johnson–Claisen rearrangement to install the (E)-configured double bond on the side chain. The proposed stereoisomer of amorfrutin D and its enantiomer have been synthesized enantioselectively from the same starting material, both in nine steps, using the CBS asymmetric reduction as the key step.

Original languageEnglish
Article number151477
JournalTetrahedron Letters
Volume61
Issue number6
DOIs
Publication statusPublished - 2020 Feb 6

Keywords

  • Amorfrutin
  • CBS reduction
  • Johnson-Claisen rearrangement
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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