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

Stamos Ioannis K. | Zendy; Kelly Elyse A. | Zendy; Floss Heinz G. | Zendy; Cassady John M. | Zendy

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

Author(s) -

Stamos Ioannis K.,

Kelly Elyse A.,

Floss Heinz G.,

Cassady John M.

Publication year - 1995

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570320435

Subject(s) - chemistry , diastereomer , methylamine , enamine , alkylation , nitrogen atom , ring (chemistry) , lithium (medication) , ethylamine , hydrolysis , amine gas treating , aluminum hydride , lithium hydroxide , medicinal chemistry , lithium aluminium hydride , stereochemistry , organic chemistry , methanol , catalysis , medicine , ion , methoxide , ion exchange , endocrinology

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.

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