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

Beilstein Journal of Organic Chemistry

Vladimír Křen¹  David Biedermann¹  Jörg Heilmann²  Guozheng Huang³  Simon Schramm³  Michael Decker³ 

[1] Centre of Biotransformation and Biocatalysis, Institute of Microbiology, Czech Academy of Sciences, Videnska 1083, Prague 4, CZ-14220, Czech Republic;Lehrstuhl für Pharmazeutische Biologie, Institut für Pharmazie, Universität Regensburg, Universitätsstraße 31, D-93053 Regensburg, Germany;Pharmazeutische und Medizinische Chemie, Institut für Pharmazie und Lebensmittelchemie, Julius-Maximilians-Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany;

关键词: dehydration;    flavonoid;    hydnocarpin;    Mitsunobu;    silybin;   

DOI  :  10.3762/bjoc.12.66

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown