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.

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

Pharmazeutische und Medizinische Chemie Institut für Pharmazie und Lebensmittelchemie Julius Maximilians Universität Würzburg Am Hubland D 97074 Würzburg Germany; College of Life and Environmental Sciences Shanghai Normal University Shanghai P R China

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Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners