A concise first total synthesis of narceine imide.
A concise and efficient total synthesis of alkaloid narceine imide is disclosed. The key steps are based upon the sequential construction of the isoindolinone template followed by metalation and coupling with an isoquinolinium salt. Subsequent E1cb elimination enables the creation of the arylmethylene unit with the concomitant formation of the dimethylaminoethyl chain and ultimate deprotection completes the synthesis of the natural product.
Lamblin
Marc
M
UMR 8009 Chimie Organique et Macromoléculaire, LCOP, Bâtiment C3(2), Université des Sciences et Technologies de Lille, 59655 Villeneuve d'Ascq Cedex, France.
Couture
Axel
A
Deniau
Eric
E
Grandclaudon
Pierre
P
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D052117:Benzodioxoles / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007212:Indolizines / Q000737:chemistry; D007769:Lactams / Q000737:chemistry
D000470:Alkaloids; D052117:Benzodioxoles; D026121:Indole Alkaloids; D007212:Indolizines; D007769:Lactams; C521097:narceine imide