SYNTHESIS AND ANALYSIS OF COMPOUNDS HAVING THE SKELETON OF ERGOT ALKALOIDS WITH THE NITROGEN ATOM IN THE D-RING TRANSPOSED

Authors
STAMOS IK KELLY EA FLOSS HG CASSADY JM
Citation
Ik. Stamos et al., SYNTHESIS AND ANALYSIS OF COMPOUNDS HAVING THE SKELETON OF ERGOT ALKALOIDS WITH THE NITROGEN ATOM IN THE D-RING TRANSPOSED, Journal of heterocyclic chemistry, 32(4), 1995, pp. 1303-1308
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
32
Issue
4
Year of publication
1995
Pages
1303 - 1308
Database
ISI
SICI code
0022-152X(1995)32:4<1303:SAAOCH>2.0.ZU;2-V
Abstract
Alkylation-amination of the enamine 2 in the presence of ethyl alpha,a lpha-bis(dibromomethyl)acetate, triethylamine, and methylamine lead to the construction of the aza-transposed ergoline 3. Sequential reducti on, hydrolysis, reesterification, and indolization of 3, produced thre e diastereomers of 6. The structure of these three diastereomers was a ssigned on the basis of nmr and ir spectral analysis to be (alpha-cis) syn, (beta-cis) anti, and (alpha-trans) syn. The isomer (beta-cis) an ti was reduced with lithium aluminum hydride to the corresponding alco hol.