37686-86-5Relevant academic research and scientific papers
Molecular structure of cis- and trans-tergurides
Husa, Michal,Kratochvil, Bohumil,Sedmera, Petr,Havlicek, Vladimir,Votavova, Hana,Cvak, Ladislav,Bulej, Petr,Jegorov, Alexandr
, p. 425 - 433 (2007/10/03)
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].
STRIKING INFLUENCE OF THE REACTION CONDITIONS ON THE STEREOSELECTIVITY IN ELECTROPHILIC SUBSTITUTION OF A 10-LITHIO-ERGOLINYL-UREA
Sauer, Gerhard,Schroeter, Bernd,Kuenzer, Hermann
, p. 6429 - 6432 (2007/10/02)
The regioselectivity of the deprotonation of the 8α-ergolinyl-urea 1 (terguride) depends on the substituent at the indole nitrogen.A tert.-butyl-dimethylsilyl (TBDMS) protecting group facilitates the removal of the angular benzylic proton in position 10.The reaction of the 10-lithio compound 5 with electrophiles affords cis or trans fused products, depending on reagent and reaction conditions.
