Collect. Czech. Chem. Commun. 1998, 63, 425-433

Molecular Structure of cis- and trans-Tergurides

Michal Hušáka, Bohumil Kratochvíla, Petr Sedmerab, Vladimír Havlíčekb, Hana Votavovác, Ladislav Cvakd, Petr Bulejd and Alexandr Jegorove

a Department of Solid State Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic
b Institute of Microbiology, 142 20 Prague 4, Czech Republic
c Institute of Organic Chemistry and Biochemistry, 166 10 Prague 6, Czech Republic
d Galena Co., R.& D., 747 70 Opava-Komárov, Czech Republic
e Galena Co., Research Unit, Branišovská 31, 370 05 České Budějovice, Czech Republic


Four isomers of terguride, a semisynthetic ergot alkaloid derivative, have been prepared by catalytic hydrogenation of (5R,8S)- and (5S,8S)-lisuride [1,1-diethyl-3-(6-methyl-8-ergolenyl)urea]. Relative stereochemistry of the isomers is based on NMR and CD spectra. Absolute configuration of all the series has been confirmed by the X-ray crystal structure determination of (5R,8S,10S)-terguride 2-bromobenzoate [1,1-diethyl-3-(6-methyl-8-isoergolenyl)urea, cis-dihydrolisuride].

Keywords: Tergurides; Ergot alkaloids; Crystal structure determination; NMR spectroscopy; Absolute configuration.