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

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, hy...

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Published inBeilstein journal of organic chemistry Vol. 12; no. 1; pp. 662 - 669
Main Authors Huang, Guozheng, Schramm, Simon, Heilmann, Jörg, Biedermann, David, Křen, Vladimír, Decker, Michael
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 08.04.2016
Beilstein-Institut
Subjects
Chemistry
dehydration
flavonoid
Full Research Paper
hydnocarpin
Mitsunobu
silybin
dehydration
Mitsunobu
flavonoid
hydnocarpin
silybin
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ISSN1860-5397
2195-951X
1860-5397
DOI10.3762/bjoc.12.66

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Summary: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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ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.12.66