First synthesis of (±)-pseudohygrophorone A12, an anti-fungal cyclohexenone derivative isolated from Hygrophorus abieticola

Yuzuki Yamamoto; Naoki Mori; Hidenori Watanabe; Hirosato Takikawa

doi:10.1016/j.tetlet.2018.08.027

First synthesis of (±)-pseudohygrophorone A¹², an anti-fungal cyclohexenone derivative isolated from Hygrophorus abieticola

Yuzuki Yamamoto, Naoki Mori, Hidenori Watanabe, Hirosato Takikawa

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

Pseudohygrophorones A¹² and B¹² are cyclohexenone derivatives isolated from Hygrophorus abieticola (Basidiomycete) as anti-phytopathogenic compounds. In this study, the first synthesis of (±)-pseudohygrophorones A¹² is reported, utilizing Michael–aldol cascade reaction for constructing the 3,3-dimethyl-2,4-dioxabicyclo[3.1.1]nonan-9-one skeleton and the diastereoselective addition of alkyllithium to the one-side blocked ketone as the key steps.

Original language	English
Pages (from-to)	3503-3505
Number of pages	3
Journal	Tetrahedron Letters
Volume	59
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2018.08.027
Publication status	Published - 2018 Sep 19
Externally published	Yes

Keywords

Anti-phytopathogenic activity
Diastereoselectivity
Hygrophorus abieticola
Michael–aldol cascade reaction
Pseudohygrophorones

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2018.08.027

Cite this

@article{1a6e65b680064641ad4595a167e4bb7a,

title = "First synthesis of (±)-pseudohygrophorone A12, an anti-fungal cyclohexenone derivative isolated from Hygrophorus abieticola",

abstract = "Pseudohygrophorones A12 and B12 are cyclohexenone derivatives isolated from Hygrophorus abieticola (Basidiomycete) as anti-phytopathogenic compounds. In this study, the first synthesis of (±)-pseudohygrophorones A12 is reported, utilizing Michael–aldol cascade reaction for constructing the 3,3-dimethyl-2,4-dioxabicyclo[3.1.1]nonan-9-one skeleton and the diastereoselective addition of alkyllithium to the one-side blocked ketone as the key steps.",

keywords = "Anti-phytopathogenic activity, Diastereoselectivity, Hygrophorus abieticola, Michael–aldol cascade reaction, Pseudohygrophorones",

author = "Yuzuki Yamamoto and Naoki Mori and Hidenori Watanabe and Hirosato Takikawa",

note = "Funding Information: This work was financially supported in part by Sumitomo Chemical Co., Ltd . We also thank Prof. K. Ishigami (Tokyo University of Agriculture) for his helpful discussion in computational studies. Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd Copyright: Copyright 2018 Elsevier B.V., All rights reserved.",

year = "2018",

month = sep,

day = "19",

doi = "10.1016/j.tetlet.2018.08.027",

language = "English",

volume = "59",

pages = "3503--3505",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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T1 - First synthesis of (±)-pseudohygrophorone A12, an anti-fungal cyclohexenone derivative isolated from Hygrophorus abieticola

AU - Yamamoto, Yuzuki

AU - Mori, Naoki

AU - Watanabe, Hidenori

AU - Takikawa, Hirosato

N1 - Funding Information: This work was financially supported in part by Sumitomo Chemical Co., Ltd . We also thank Prof. K. Ishigami (Tokyo University of Agriculture) for his helpful discussion in computational studies. Publisher Copyright: © 2018 Elsevier Ltd Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

PY - 2018/9/19

Y1 - 2018/9/19

N2 - Pseudohygrophorones A12 and B12 are cyclohexenone derivatives isolated from Hygrophorus abieticola (Basidiomycete) as anti-phytopathogenic compounds. In this study, the first synthesis of (±)-pseudohygrophorones A12 is reported, utilizing Michael–aldol cascade reaction for constructing the 3,3-dimethyl-2,4-dioxabicyclo[3.1.1]nonan-9-one skeleton and the diastereoselective addition of alkyllithium to the one-side blocked ketone as the key steps.

AB - Pseudohygrophorones A12 and B12 are cyclohexenone derivatives isolated from Hygrophorus abieticola (Basidiomycete) as anti-phytopathogenic compounds. In this study, the first synthesis of (±)-pseudohygrophorones A12 is reported, utilizing Michael–aldol cascade reaction for constructing the 3,3-dimethyl-2,4-dioxabicyclo[3.1.1]nonan-9-one skeleton and the diastereoselective addition of alkyllithium to the one-side blocked ketone as the key steps.

KW - Anti-phytopathogenic activity

KW - Diastereoselectivity

KW - Hygrophorus abieticola

KW - Michael–aldol cascade reaction

KW - Pseudohygrophorones

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JO - Tetrahedron Letters

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