Synthesis and structural revision of an indanone isolated from Triphyophyllum peltatum

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

doi:10.1016/j.tetlet.2019.151494

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 journal › Article › peer-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 language	English
Article number	151494
Journal	Tetrahedron Letters
Volume	61
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2019.151494
Publication status	Published - 2020 Feb 13
Externally published	Yes

Keywords

1,4-Naphthoquinone
Indanone
Skeletal rearrangement
Structural revision

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis and structural revision of an indanone isolated from Triphyophyllum peltatum",

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.",

keywords = "1,4-Naphthoquinone, Indanone, Skeletal rearrangement, Structural revision",

author = "Yunosuke Ishii and Motohiro Ota and Shogo Kamo and Shusuke Tomoshige and Kazunori Tsubaki and Kouji Kuramochi",

note = "Funding Information: This study was supported by Japan Society for the Promotion of Science (JSPS) KAKENHI (No. 18K19185 ). Appendix A ",

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doi = "10.1016/j.tetlet.2019.151494",

language = "English",

volume = "61",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis and structural revision of an indanone isolated from Triphyophyllum peltatum

AU - Ishii, Yunosuke

AU - Ota, Motohiro

AU - Kamo, Shogo

AU - Tomoshige, Shusuke

AU - Tsubaki, Kazunori

AU - Kuramochi, Kouji

N1 - Funding Information: This study was supported by Japan Society for the Promotion of Science (JSPS) KAKENHI (No. 18K19185 ). Appendix A

PY - 2020/2/13

Y1 - 2020/2/13

N2 - 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.

AB - 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.

KW - 1,4-Naphthoquinone

KW - Indanone

KW - Skeletal rearrangement

KW - Structural revision

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