Jiangrine-like scaffolds from biorenewable platforms

Abstract Dihydrolevoglucosenone (DLGO) and amino aldehydes undergo an aldol reaction mediated by the heterogenous base KF-alumina; exposure of the aldol adducts to hydrogenation followed by silica gel results in the formation of pyrrole-2-carbaldehydes bearing the jiangrine alkaloid scaffold. KF-alumina is also an effective base in the aldol condensation between DLGO and aliphatic/aromatic aldehydes, with no self-aldol reaction apparent.