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

Huang, Guozheng ; Schramm, Simon ; Heilmann, Jörg ; Biedermann, David ; Křen, Vladimír ; Decker, Michael



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.


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