Synthesis of fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside based on site-selective deacetylation and deoxygenation

Ryuji Tsunekawa; Kengo Hanaya; Shuhei Higashibayashi; Takeshi Sugai

doi:10.1080/09168451.2018.1467263

Synthesis of fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside based on site-selective deacetylation and deoxygenation

Ryuji Tsunekawa, Kengo Hanaya, Shuhei Higashibayashi, Takeshi Sugai

School of Pharmaceutical Sciences

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

4 Citations (Scopus)

Abstract

Fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside were synthesized from commercially available quercetin and naringin in five steps. The key steps are site-selective deacetylation and subsequent deoxygenation. The target molecules were obtained in 37% and 23% yields from the starting materials, respectively.

Original language	English
Pages (from-to)	1316-1322
Number of pages	7
Journal	Bioscience, Biotechnology and Biochemistry
Volume	82
Issue number	8
DOIs	https://doi.org/10.1080/09168451.2018.1467263
Publication status	Published - 2018

Keywords

Deoxygenation
Dihydrochalcone glycoside
Fisetin
Site-selective deacetylation
Triflate

ASJC Scopus subject areas

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

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Synthesis of fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside based on site-selective deacetylation and deoxygenation. / Tsunekawa, Ryuji; Hanaya, Kengo ; Higashibayashi, Shuhei ; Sugai, Takeshi.

In: Bioscience, Biotechnology and Biochemistry, Vol. 82, No. 8, 2018, p. 1316-1322.

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

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abstract = "Fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside were synthesized from commercially available quercetin and naringin in five steps. The key steps are site-selective deacetylation and subsequent deoxygenation. The target molecules were obtained in 37% and 23% yields from the starting materials, respectively.",

keywords = "Deoxygenation, Dihydrochalcone glycoside, Fisetin, Site-selective deacetylation, Triflate",

author = "Ryuji Tsunekawa and Kengo Hanaya and Shuhei Higashibayashi and Takeshi Sugai",

note = "Funding Information: This work was supported by JSPS KAKENHI (16K21362) for K. H. and by a grant from a public interest incorporated foundation “Amano Institute of Technology” for T. S. and are gratefully acknowledged with thanks.",

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AU - Tsunekawa, Ryuji

AU - Hanaya, Kengo

AU - Higashibayashi, Shuhei

AU - Sugai, Takeshi

N1 - Funding Information: This work was supported by JSPS KAKENHI (16K21362) for K. H. and by a grant from a public interest incorporated foundation “Amano Institute of Technology” for T. S. and are gratefully acknowledged with thanks.

PY - 2018

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AB - Fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside were synthesized from commercially available quercetin and naringin in five steps. The key steps are site-selective deacetylation and subsequent deoxygenation. The target molecules were obtained in 37% and 23% yields from the starting materials, respectively.

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KW - Dihydrochalcone glycoside

KW - Fisetin

KW - Site-selective deacetylation

KW - Triflate

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