An efficient synthesis of daidzein, dimethyldaidzein, and isoformononetin

Kyle F. Biegasiewicz; Jeffrey D.St Denis; Vincent M. Carroll; Ronny Priefer

doi:10.1016/j.tetlet.2010.06.078

An efficient synthesis of daidzein, dimethyldaidzein, and isoformononetin

Kyle F. Biegasiewicz, Jeffrey D.St Denis, Vincent M. Carroll, Ronny Priefer

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

25 Scopus citations

Abstract

Synthesis of the soy isoflavone, daidzein, and its derivatives, isoformononetin and dimethyldaidzein, through utilization of a novel synthetic pathway is reported. This synthesis employs an enamine addition and O-methylation of 2,4-dihydroxyacetophenone, a subsequent ring closure and iodination, followed by a Suzuki coupling with PEG 10000. Demethylation of either isoformononetin or dimethyldaidzein afforded daidzein.

Original language	English (US)
Pages (from-to)	4408-4410
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2010.06.078
State	Published - Aug 18 2010
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.06.078

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title = "An efficient synthesis of daidzein, dimethyldaidzein, and isoformononetin",

abstract = "Synthesis of the soy isoflavone, daidzein, and its derivatives, isoformononetin and dimethyldaidzein, through utilization of a novel synthetic pathway is reported. This synthesis employs an enamine addition and O-methylation of 2,4-dihydroxyacetophenone, a subsequent ring closure and iodination, followed by a Suzuki coupling with PEG 10000. Demethylation of either isoformononetin or dimethyldaidzein afforded daidzein.",

author = "Biegasiewicz, {Kyle F.} and Denis, {Jeffrey D.St} and Carroll, {Vincent M.} and Ronny Priefer",

note = "Funding Information: The authors would like to thank the Niagara University Academic Center for Integrated Science and the Rochester Academy of Science for the financial support.",

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doi = "10.1016/j.tetlet.2010.06.078",

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T1 - An efficient synthesis of daidzein, dimethyldaidzein, and isoformononetin

AU - Biegasiewicz, Kyle F.

AU - Denis, Jeffrey D.St

AU - Carroll, Vincent M.

AU - Priefer, Ronny

N1 - Funding Information: The authors would like to thank the Niagara University Academic Center for Integrated Science and the Rochester Academy of Science for the financial support.

PY - 2010/8/18

Y1 - 2010/8/18

N2 - Synthesis of the soy isoflavone, daidzein, and its derivatives, isoformononetin and dimethyldaidzein, through utilization of a novel synthetic pathway is reported. This synthesis employs an enamine addition and O-methylation of 2,4-dihydroxyacetophenone, a subsequent ring closure and iodination, followed by a Suzuki coupling with PEG 10000. Demethylation of either isoformononetin or dimethyldaidzein afforded daidzein.

AB - Synthesis of the soy isoflavone, daidzein, and its derivatives, isoformononetin and dimethyldaidzein, through utilization of a novel synthetic pathway is reported. This synthesis employs an enamine addition and O-methylation of 2,4-dihydroxyacetophenone, a subsequent ring closure and iodination, followed by a Suzuki coupling with PEG 10000. Demethylation of either isoformononetin or dimethyldaidzein afforded daidzein.

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M3 - Article

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SN - 0040-4039

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SP - 4408

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

An efficient synthesis of daidzein, dimethyldaidzein, and isoformononetin

Abstract

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