Premium
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.