Selective reduction of peptidic ergot alkaloids

Citation
L. Cvak et al., Selective reduction of peptidic ergot alkaloids, COLL CZECH, 65(11), 2000, pp. 1762-1776
Citations number
30
Categorie Soggetti
Chemistry
Journal title
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
ISSN journal
00100765 → ACNP
Volume
65
Issue
11
Year of publication
2000
Pages
1762 - 1776
Database
ISI
SICI code
0010-0765(200011)65:11<1762:SROPEA>2.0.ZU;2-D
Abstract
Five 6'-deoxoergopeptines were prepared in 51-68% yield by selective reduct ion of parent alkaloids with lithium aluminium hydride in tetrahydrofuran a t low temperature. New compounds were characterized by mass spectrometry an d NMR spectroscopy. The conformation of the peptide part in starting compou nds and reduced derivatives is discussed on the basis of crystal structure determination of 6'-deoxo-9,10-dihydroergotamine dihydrate butan-2-one solv ate as a representative member of the series.