ISSN:
0947-3440
Keywords:
Ene reaction
;
Benzo[b]quinolidines
;
Azepino[1,2-b]isoquinolines
;
Lewis acid catalysis
;
Nitrogen heterocycles
;
Cyclizations
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
(L)-Phenylalanine 4 can be converted to N-(4-methyl-3-pentenyl)tetrahydrosisoquinoline-3-carbaldehyde 10 and the corresponding homologous aldehyde 19 in 4 and 5 steps, respectively, by employing the Pictet-Spengler reaction as the key step. After Lewis acid catalyzed cyclization of 10 and 19 the cis-configured 1-hydroxybenzo[b]quinolizidine 21a and 11-hydroxyazepino[1,2-b]isoquinoline 22a were obtained with high diastereoselectivities. Compound 21a, which was characterized by X-ray structure analysis, displays a fishbone pattern of endless zig-zag chains connected via intermolecular hydrogen bonds in the solid state.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970314
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