Synthesis and biological properties of tensyuic acids B, C, and E, and investigation of the optical purity of natural tensyuic acid B

Takanori Matsumaru, Toshiaki Sunazuka, Tomoyasu Hirose, Aki Ishiyama, Miyuki Namatame, Takashi Fukuda, Hiroshi Tomoda, Kazuhiko Otoguro, Satoshi Omura

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6 Citations (Scopus)

Abstract

The first, concise total synthesis of (±)-tensyuic acids B, C, and E, using chemoselective formal SN2′ type Grignard reactions and selective esterification, is described. In addition, the optical purity of natural (±)-tensyuic acid B was determined using Chirabite-AR. Synthetic tensyuic acids, together with their intermediate compounds, were found to possess useful bioactive properties, with some of them showing potent activity against Trypanosoma brucei brucei strain GUTat 3.1.

Original languageEnglish
Pages (from-to)7369-7377
Number of pages9
JournalTetrahedron
Volume64
Issue number30-31
DOIs
Publication statusPublished - 2008 Jul 21
Externally publishedYes

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Keywords

  • Anti-trypanosomal activity
  • Chirabite-AR
  • Formal S2 reaction
  • Selective esterification
  • Tensyic acid
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Matsumaru, T., Sunazuka, T., Hirose, T., Ishiyama, A., Namatame, M., Fukuda, T., Tomoda, H., Otoguro, K., & Omura, S. (2008). Synthesis and biological properties of tensyuic acids B, C, and E, and investigation of the optical purity of natural tensyuic acid B. Tetrahedron, 64(30-31), 7369-7377. https://doi.org/10.1016/j.tet.2008.05.035