A novel Maillard‐type condensation between a primary amine derived from D‐mannitol and a dihydropyranone, was used as a key step to access the unusual morpholine‐spiroketal acortatarin A. The synthetic approach also enabled access to a C‐2 analogue of acortatarin A, and can be used for the synthesis of related 2‐formylpyrrole natural products.
First described in the late 1960s, N-alkylsulfonylimines are heterocumulenes that participate in reactions with a range of 1,3-dipoles to afford interesting 3-, 4-, 5-, and 6-membered heterocycles. The distribution of adducts obtained suggests that multistage, stepwise mechanistic pathways rather than a concerted process are in operation.
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.