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Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

Please always quote using this URN: urn:nbn:de:bvb:20-opus-160986
  • Various Mitsunobu conditions were investigated for a series of flavonolignans (silybin A, silybin B, isosilybin A, and silychristin A) to achieve either selective esterification in position C-23 or dehydration in a one-pot reaction yielding the biologically important enantiomers of hydnocarpin D, hydnocarpin and isohydnocarpin, respectively. This represents the only one-pot semi-synthetic method to access these flavonolignans in high yields.

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Author: Guozheng Huang, Simon Schramm, Jörg Heilmann, David Biedermann, Vladimír Kren, Michael Decker
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Pharmazie und Lebensmittelchemie
Parent Title (English):Beilstein Journal of Organic Chemistry
Year of Completion:2016
Source:Beilstein Journal of Organic Chemistry 2016, 12, 662–669. doi:10.3762/bjoc.12.66
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Tag:Mitsunobu; dehydration; flavonoid; hydnocarpin; silybin
Release Date:2018/07/10
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung