Synthesis and structural revision of an indanone isolated from Triphyophyllum peltatum

Yunosuke Ishii, Motohiro Ota, Shogo Kamo, Shusuke Tomoshige, Kazunori Tsubaki, Kouji Kuramochi

Research output: Contribution to journalArticlepeer-review

Abstract

In this paper, skeletal rearrangements of 2-hydroxy-3-methyl-1,4-naphthoquinones to indanones are reported. The application of this reaction to the synthesis of an indanone isolated from root cultures of the West African liana Triphyophyllum peltatum is described. The spectroscopic data of this synthetic indanone are different from those reported for the natural product, indicating that the reported structure is incorrect. The structure was unambiguously revised through the synthesis of the compound with spectroscopic data identical to the natural product. A biosynthetic conversion of droserone, 3,5-dihydroxy-2-methyl-1,4-naphthoquinone, to this indanone is also proposed.

Original languageEnglish
Article number151494
JournalTetrahedron Letters
Volume61
Issue number7
DOIs
Publication statusPublished - 2020 Feb 13
Externally publishedYes

Keywords

  • 1,4-Naphthoquinone
  • Indanone
  • Skeletal rearrangement
  • Structural revision

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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