Diverse 1,2- and 1,2,5-substituted pyrroles were efficiently prepared through a regioselective functionalization of 2-formylpyr-role (<strong>5a</strong>). This methodology was applied for the first total synthesis of pyrrolemarumine (<strong>4b</strong>), the aglycone of the corresponding natural pyr-role alkaloid 4”-O-a-L-rhamnopyranoside. The synthesis of <strong>4b</strong> was achieved starting from 5a through a seven-step process in 28% over-all yield.
The selective functionalization of 2-formylpyrrole to provide diverse 1,2-and 1,2,5-substituted pyrroles is described. These compounds were used as versatile building blocks in a divergent synthesis of biologically valuable aza-bycyclic skeletons, such as pyrrolizine and pyrrolizidine derivatives. These bicycles were prepared following metalfree cascade synthetic approaches via regioselective intramolecular 1,3dipolar cycloadditions and stereoselective Knoevenagel/Michael/ cyclization with dimethyl malonate.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.