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

Huang, Guozheng and Schramm, Simon and Heilmann, Joerg and Biedermann, David and Kren, Vladimir and Decker, Michael (2016) Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 12. pp. 662-669. ISSN 1860-5397,

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: TACRINE-SILIBININ CODRUG; IN-VITRO; SILYBIN; WIGHTIANA; ALCOHOLS; dehydration; flavonoid; hydnocarpin; Mitsunobu; silybin
Subjects: 600 Technology > 615 Pharmacy
Divisions: Chemistry and Pharmacy > Institute of Pharmacy
Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann)
Depositing User: Dr. Gernot Deinzer
Date Deposited: 21 Mar 2019 07:52
Last Modified: 21 Mar 2019 07:52
URI: https://pred.uni-regensburg.de/id/eprint/3088

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