Total synthesis of the proposed structure for pochonicine and determination of its absolute configuration

Yujiro Kitamura, Hiroyuki Koshino, Takemichi Nakamura, Aya Tsuchida, Teruhiko Nitoda, Hiroshi Kanzaki, Koji Matsuoka, Shunya Takahashi

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19 Citations (Scopus)

Abstract

Pochonicine is a polyhydroxylated pyrrolizidine alkaloid with a powerful inhibitory activity against β-Nacetylglucosaminidases. The proposed structure for pochonicine and the three diastereomers concerning its C-1 and/or C-3 positions were synthesized from N-acetyl-D-glucosamine through construction of the pyrrolizidine skeleton by two intramolecular amino cyclizations as key steps. This synthetic study not only revised the structure of the natural product to the corresponding 1,3-di-epi-form but also determined the absolute configuration as 1R, 3S, 5R, 6R, 7S, 7aR.

Original languageEnglish
Pages (from-to)1456-1459
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number11
DOIs
Publication statusPublished - Mar 13 2013

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Keywords

  • D-Allopyranoside
  • GlcNAcase inhibitor
  • N-Acetyl-D-glucosamine
  • Pochonicine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Kitamura, Y., Koshino, H., Nakamura, T., Tsuchida, A., Nitoda, T., Kanzaki, H., Matsuoka, K., & Takahashi, S. (2013). Total synthesis of the proposed structure for pochonicine and determination of its absolute configuration. Tetrahedron Letters, 54(11), 1456-1459. https://doi.org/10.1016/j.tetlet.2013.01.015