Synthesis and analysis of compounds having the skeleton of ergot alkaloids with the nitrogen atom in the D-ring transposed

Autor:	John M. Cassady, Elyse A. Kelly, Heinz G. Floss, Ioannis K. Stamos
Rok vydání:	1995
Předmět:	Methylamine Stereochemistry Organic Chemistry Diastereomer chemistry.chemical_element Alcohol Ergoline Enamine chemistry.chemical_compound Hydrolysis chemistry Nitrogen atom medicine Lithium medicine.drug
Zdroj:	Journal of Heterocyclic Chemistry. 32:1303-1308
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570320435
Popis:	Alkylation-amination of the enamine 2 in the presence of ethyl α,α-bis(dibromomethyl)acetate, triethyl-amine, and methylamine lead to the construction of the aza-transposed ergoline 3. Sequential reduction, hydrolysis, reesterification, and indolization of 3, produced three diastereomers of 6. The structure of these three diastereomers was assigned on the basis of nmr and ir spectral analysis to be (α-cis) syn, (β-cis) anti, and (α-trans) syn. The isomer (β-cis) anti was reduced with lithium aluminum hydride to the corresponding alcohol.
Databáze:	OpenAIRE
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