Total synthesis of an anti-Helicobacter pylori agent, actinopyrone A

Seijiro Hosokawa, Kazuya Yokota, Keisuke Imamura, Yasuaki Suzuki, Masataka Kawarasaki, Kuniaki Tatsuta

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23 Citations (Scopus)

Abstract

Actinopyrone A, an anti-Helicobacter pylori agent, was synthesized in nine steps from a silyl dienol ether. A vinylogous anti-aldol was stereoselectively synthesized by our developed remote stereoinduction methodology; coupling of this with a sulfone and a phosphonate species led to the construction of a vinylpyrone compound. This was submitted to reductive de-conjugation to give actinopyrone A. The absolute stereochemistry of actinopyrone A was determined to have the configuration 14R,15R.

Original languageEnglish
Pages (from-to)1415-1421
Number of pages7
JournalChemistry - An Asian Journal
Volume3
Issue number8-9
DOIs
Publication statusPublished - 2008 Sep 1

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Keywords

  • Actinopyrone A
  • Aldol reaction
  • Remote stereoinduction
  • Structural determination
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Cite this

Hosokawa, S., Yokota, K., Imamura, K., Suzuki, Y., Kawarasaki, M., & Tatsuta, K. (2008). Total synthesis of an anti-Helicobacter pylori agent, actinopyrone A. Chemistry - An Asian Journal, 3(8-9), 1415-1421. https://doi.org/10.1002/asia.200800109