1114515-63-7Relevant academic research and scientific papers
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
Ishihara, Yuhsuke,Azuma, Shuhei,Choshi, Tominari,Kohno, Kakujirou,Ono, Kanako,Tsutsumi, Hiroyuki,Ishizu, Takashi,Hibino, Satoshi
, p. 1320 - 1333 (2011/04/16)
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).
A new synthesis of the benzo[c]phenanthridines nornitidine, noravicine, and isodecarine, based on a microwave-assisted electrocyclic reaction of the aza 6π-electron system
Kohno, Kakujiro,Azuma, Shuhei,Choshi, Tominari,Nobuhiro, Junko,Hibino, Satoshi
scheme or table, p. 590 - 592 (2009/05/27)
A new and versatile synthetic route to a benzophenanthridine alkaloid was developed by a bond formation between C4b and N5 on the benzo[c]phenanthridine nucleus, using a microwave-assisted electrocyclic reaction of the aza 6π-electron system. This strateg
