Easy access to both enantiomers of 5-hydroxyequol and 3-(4-hydroxyphenyl)chroman-8-ol

5-Hydroxyequol, a biologically active isoflavone metabolite from genistein, has been synthesized enantioselectively from 3-(2,4,6-trimethoxyphenyl)propanal by using MacMillans’ asymmetric α -arylation protocol of carbonyl compound. (S)- and (R)-5-Hydroxyequols have been obtained in 90% and 88% ee, r...

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Autores principales:	Takahito Uemura, Motohiro Sonoda, Shinji Tanimori
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2021
Materias:	5-Hydroxyequol Asymmetric synthesis α-Arylation Isoflavone MacMillan’s catalyst Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/b20805afb0e248c1ad06a0ee75183be5
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id	oai:doaj.org-article:b20805afb0e248c1ad06a0ee75183be5
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spelling	oai:doaj.org-article:b20805afb0e248c1ad06a0ee75183be52021-12-04T04:33:56ZEasy access to both enantiomers of 5-hydroxyequol and 3-(4-hydroxyphenyl)chroman-8-ol2211-715610.1016/j.rechem.2021.100252https://doaj.org/article/b20805afb0e248c1ad06a0ee75183be52021-01-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S2211715621001570https://doaj.org/toc/2211-71565-Hydroxyequol, a biologically active isoflavone metabolite from genistein, has been synthesized enantioselectively from 3-(2,4,6-trimethoxyphenyl)propanal by using MacMillans’ asymmetric α -arylation protocol of carbonyl compound. (S)- and (R)-5-Hydroxyequols have been obtained in 90% and 88% ee, respectively, by employing enantiomeric imidazolidinone catalysts derived from D- and L-phenylglycines. The absolute configuration of natural 5-hydroxyequol has been definitely assigned to (S)-stereochemistry. (S)- And (R)-3-(4-hydroxyphenyl)chroman-8-ol, an unnatural equol isomer, have also been synthesized for the first time in 76% and 84% ee, respectively.Takahito UemuraMotohiro SonodaShinji TanimoriElsevierarticle5-HydroxyequolAsymmetric synthesisα-ArylationIsoflavoneMacMillan’s catalystChemistryQD1-999ENResults in Chemistry, Vol 3, Iss , Pp 100252- (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	5-Hydroxyequol Asymmetric synthesis α-Arylation Isoflavone MacMillan’s catalyst Chemistry QD1-999
spellingShingle	5-Hydroxyequol Asymmetric synthesis α-Arylation Isoflavone MacMillan’s catalyst Chemistry QD1-999 Takahito Uemura Motohiro Sonoda Shinji Tanimori Easy access to both enantiomers of 5-hydroxyequol and 3-(4-hydroxyphenyl)chroman-8-ol
description	5-Hydroxyequol, a biologically active isoflavone metabolite from genistein, has been synthesized enantioselectively from 3-(2,4,6-trimethoxyphenyl)propanal by using MacMillans’ asymmetric α -arylation protocol of carbonyl compound. (S)- and (R)-5-Hydroxyequols have been obtained in 90% and 88% ee, respectively, by employing enantiomeric imidazolidinone catalysts derived from D- and L-phenylglycines. The absolute configuration of natural 5-hydroxyequol has been definitely assigned to (S)-stereochemistry. (S)- And (R)-3-(4-hydroxyphenyl)chroman-8-ol, an unnatural equol isomer, have also been synthesized for the first time in 76% and 84% ee, respectively.
format	article
author	Takahito Uemura Motohiro Sonoda Shinji Tanimori
author_facet	Takahito Uemura Motohiro Sonoda Shinji Tanimori
author_sort	Takahito Uemura
title	Easy access to both enantiomers of 5-hydroxyequol and 3-(4-hydroxyphenyl)chroman-8-ol
title_short	Easy access to both enantiomers of 5-hydroxyequol and 3-(4-hydroxyphenyl)chroman-8-ol
title_full	Easy access to both enantiomers of 5-hydroxyequol and 3-(4-hydroxyphenyl)chroman-8-ol
title_fullStr	Easy access to both enantiomers of 5-hydroxyequol and 3-(4-hydroxyphenyl)chroman-8-ol
title_full_unstemmed	Easy access to both enantiomers of 5-hydroxyequol and 3-(4-hydroxyphenyl)chroman-8-ol
title_sort	easy access to both enantiomers of 5-hydroxyequol and 3-(4-hydroxyphenyl)chroman-8-ol
publisher	Elsevier
publishDate	2021
url	https://doaj.org/article/b20805afb0e248c1ad06a0ee75183be5
work_keys_str_mv	AT takahitouemura easyaccesstobothenantiomersof5hydroxyequoland34hydroxyphenylchroman8ol AT motohirosonoda easyaccesstobothenantiomersof5hydroxyequoland34hydroxyphenylchroman8ol AT shinjitanimori easyaccesstobothenantiomersof5hydroxyequoland34hydroxyphenylchroman8ol
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Easy access to both enantiomers of 5-hydroxyequol and 3-(4-hydroxyphenyl)chroman-8-ol

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