Collect. Czech. Chem. Commun. 2000, 65, 1762-1776

Selective Reduction of Peptidic Ergot Alkaloids

Ladislav Cvaka, Josef Stuchlíka, Magdalena Schreiberováa, Petr Sedmerab,*, Vladimír Havlíčekb, Miroslav Fliegerb, Jan Čejkac, Bohumil Kratochvílc and Alexandr Jegorovd

a Galena Co., R&D, 747 70 Opava-Komárov, Czech Republic
b Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, 142 20 Prague 4, Czech Republic
c Department of Solid State Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
d Galena Co., Research Unit, Branišovská 31, 370 05 České Budějovice, Czech Republic


Five 6'-deoxoergopeptines were prepared in 51-68% yield by selective reduction of parent alkaloids with lithium aluminium hydride in tetrahydrofuran at low temperature. New compounds were characterized by mass spectrometry and NMR spectroscopy. The conformation of the peptide part in starting compounds and reduced derivatives is discussed on the basis of crystal structure determination of 6'-deoxo-9,10-dihydroergotamine dihydrate butan-2-one solvate as a representative member of the series.

Keywords: Indole alkaloids; Ergot alkaloids; Ergopeptines; Peptides; Reductions; NMR spectroscopy; Mass spectrometry; Crystal structure determination; X-Ray diffraction.

References: 30 live references.