%0 Journal Article %J ACS Omega %D 2020 %T Chemoselective ring closure of 4-(3-Methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal leading to pandalizine A %A Yadav, Mahesh B. %A Pandhade, Kailas R. %A Argade, Narshinha P. %X

Starting from methylmaleic anhydride, a facile total synthesis of pandalizine A alkaloid is described via the regioselective reduction of methylmaleimide and acid-catalyzed enolization of 4-(3-methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal followed by chemoselective intramolecular dehydrative cyclization as the key steps. It is noteworthy that the analogous model system with an additional beta-methyl group followed an alternative chemoselective intermolecular aldol condensation pathway.

%B ACS Omega %V 5 %P 859-863 %8 JAN %G eng %N 1 %9 Article %3

Foreign

%4

2.870

%R 10.1021/acsomega.9b03760