Sie befinden Sich nicht im Netzwerk der Universität Paderborn. Der Zugriff auf elektronische Ressourcen ist gegebenenfalls nur via VPN oder Shibboleth (DFN-AAI) möglich. mehr Informationen...
Total synthesis of benzo[ c]phenanthridine alkaloids based on a microwave-assisted electrocyclic reaction of the aza 6π-electron system and structural revision of broussonpapyrine
Ist Teil von
Tetrahedron, 2011-02, Vol.67 (6), p.1320-1333
Ort / Verlag
Kidlington: Elsevier Ltd
Erscheinungsjahr
2011
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
Total syntheses of the des-
N-methyl (nor) type of benzo[
c]phenanthridine alkaloids
1a–
f and
19 and benzo[
c]phenanthridine alkaloids, chelerythrine (
2d), and broussonpapyrine (
2f) were achieved. The key step was the construction of tetracyclic 10,11-dihydrobenzo[
c]phenanthridines using a microwave-assisted electrocyclic reaction of the 2-cycloalkenylbenzaldoxime methyl ether
4 as an aza 6π-electron system, which was derived in two steps from a Suzuki–Miyaura cross-coupling reaction of 2-bromobenzaldehyde
6 with 2-(3,4-dihydro-6,7-methylenedioxynaphthyl)boronic acid pinacol ester
7. In addition, the exact structure of broussonpapyrine (
2f) (2,3,9,10-tetraoxygenated type) was determined to be chelerythrine (
2d).
[Display omitted]