Total synthesis of terfestatins a and B

Shun Sugawara, Yasuhiro Meguro, Shuntaro Sato, Masaru Enomoto, Yusuke Ogura, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

Abstract

Terfestatin A, a specific inhibitor of auxin signaling, has been synthesized from a known aromatic aldehyde in 21% overall yield via five steps. The first total synthesis of terfestatin B with potent neuroprotective activity has also been accomplished in eight steps from the same aromatic aldehyde in 30% overall yield through a common intermediate. The key feature of this synthesis is the utilization of the aldehyde functionality of the starting material both as a directing group for regioselective O-protection and as a masked hydroxy group.

Original languageEnglish
Article number151891
JournalTetrahedron Letters
Volume61
Issue number21
DOIs
Publication statusPublished - 2020 May 21

Keywords

  • DWAQMWPHCVWJMI-SMTRDTIPSA-N
  • Natural product
  • Terfestatin
  • Total synthesis
  • UTRHHGVQLUCOIT-NZXWXYQFSA-N
  • p-Terphenyl

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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