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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| Auteurs principaux: | , , |
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| Format: | article |
| Langue: | EN |
| Publié: |
Elsevier
2021
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| Sujets: | |
| Accès en ligne: | https://doaj.org/article/b20805afb0e248c1ad06a0ee75183be5 |
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| Résumé: | 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. |
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