caa a22 4500 378866397 CHVBK 20180305123358.0 cr unu---uuuuu 161128e20030101xx s 000 0 eng 10.1351/pac200375020273 doi (NATIONALLICENCE)gruyter-10.1351/pac200375020273 Enantioselective synthesis and biological evaluation of a-hydroxylated lactone lignans [Elektronische Daten] [M. Sefkow, M. Raschke, C. Steiner] A short and efficient synthesis of enantiomerically pure α-hydroxylated lactone lignans starting from commercially available diisopropyl malate is presented. Stereoselective alkylation with various benzyl bromides and saponification yielded the corresponding succinic acids. Acetalization afforded the dioxolanones, which were stereoselectively alkylated. Reduction (and deprotection, where required) yielded the lactone lignans in up to 30 % overall yield. The inhibition of the proliferation of HT29 colon cancer cells was investigated. One lignane, bis-2,4,6 trimethylbenzyllactone lignan, was active (IC50 = 35 μM), whereas all other tested lignans were inactive within the investigated concentration range. © 2013 Walter de Gruyter GmbH, Berlin/Boston Sefkow M. Universität Potsdam, Institut für Chemie, Karl-Liebknecht-Strasse 24-25, D-14476 Golm, Germany aut Raschke M. Universität Jena, Lehrstuhl für Ernährungstoxikologie, Dornburger Strasse 25, D-07743 Jena, Germany aut Steiner C. Universität Jena, Lehrstuhl für Ernährungstoxikologie, Dornburger Strasse 25, D-07743 Jena, Germany aut Pure and Applied Chemistry De Gruyter 75/2-3(2003-01-01), 273-278 0033-4545 75:2-3<273 2003 75 pac https://doi.org/10.1351/pac200375020273 text/html Onlinezugriff via DOI 1 research article jats NATIONALLICENCE 856 40 https://doi.org/10.1351/pac200375020273 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Sefkow M. Universität Potsdam, Institut für Chemie, Karl-Liebknecht-Strasse 24-25, D-14476 Golm, Germany aut NATIONALLICENCE 700 1- Raschke M. Universität Jena, Lehrstuhl für Ernährungstoxikologie, Dornburger Strasse 25, D-07743 Jena, Germany aut NATIONALLICENCE 700 1- Steiner C. Universität Jena, Lehrstuhl für Ernährungstoxikologie, Dornburger Strasse 25, D-07743 Jena, Germany aut NATIONALLICENCE 773 0- Pure and Applied Chemistry De Gruyter 75/2-3(2003-01-01), 273-278 0033-4545 75:2-3<273 2003 75 pac CC0 http://creativecommons.org/publicdomain/zero/1.0 nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-gruyter