Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation

Yasunobu Yamashita; Alan Biard; Kengo Hanaya; Mitsuru Shoji; Takeshi Sugai

doi:10.1080/09168451.2017.1303362

Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation

Yasunobu Yamashita, Alan Biard, Kengo Hanaya, Mitsuru Shoji, Takeshi Sugai

School of Pharmaceutical Sciences

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

13 Citations (Scopus)

Abstract

Wogonin and astringin were synthesized from inexpensive chrysin and piceid in short steps. The key feature of these syntheses is site-selective transformation. The target molecules were obtained in 27 and 62% yields from the starting materials, respectively.

Original language	English
Pages (from-to)	1279-1284
Number of pages	6
Journal	Bioscience, Biotechnology and Biochemistry
Volume	81
Issue number	7
DOIs	https://doi.org/10.1080/09168451.2017.1303362
Publication status	Published - 2017

Keywords

Astringin
Hydroxylation
Site-selective acetylation
Site-selective deacetylation
Wogonin

ASJC Scopus subject areas

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

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10.1080/09168451.2017.1303362

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title = "Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation",

abstract = "Wogonin and astringin were synthesized from inexpensive chrysin and piceid in short steps. The key feature of these syntheses is site-selective transformation. The target molecules were obtained in 27 and 62% yields from the starting materials, respectively.",

keywords = "Astringin, Hydroxylation, Site-selective acetylation, Site-selective deacetylation, Wogonin",

author = "Yasunobu Yamashita and Alan Biard and Kengo Hanaya and Mitsuru Shoji and Takeshi Sugai",

note = "Funding Information: This work was supported by grant-aid for scientific research [grant number 26450143] and Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and is gratefully acknowledged with thanks. Publisher Copyright: {\textcopyright} 2017 Japan Society for Bioscience, Biotechnology, and Agrochemistry.",

year = "2017",

doi = "10.1080/09168451.2017.1303362",

language = "English",

volume = "81",

pages = "1279--1284",

journal = "Bioscience, Biotechnology and Biochemistry",

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publisher = "Japan Society for Bioscience Biotechnology and Agrochemistry",

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T1 - Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation

AU - Yamashita, Yasunobu

AU - Biard, Alan

AU - Hanaya, Kengo

AU - Shoji, Mitsuru

AU - Sugai, Takeshi

N1 - Funding Information: This work was supported by grant-aid for scientific research [grant number 26450143] and Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and is gratefully acknowledged with thanks. Publisher Copyright: © 2017 Japan Society for Bioscience, Biotechnology, and Agrochemistry.

PY - 2017

Y1 - 2017

N2 - Wogonin and astringin were synthesized from inexpensive chrysin and piceid in short steps. The key feature of these syntheses is site-selective transformation. The target molecules were obtained in 27 and 62% yields from the starting materials, respectively.

AB - Wogonin and astringin were synthesized from inexpensive chrysin and piceid in short steps. The key feature of these syntheses is site-selective transformation. The target molecules were obtained in 27 and 62% yields from the starting materials, respectively.

KW - Astringin

KW - Hydroxylation

KW - Site-selective acetylation

KW - Site-selective deacetylation

KW - Wogonin

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SN - 0916-8451

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EP - 1284

JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

IS - 7

ER -

Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation

Abstract

Keywords

ASJC Scopus subject areas

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