Organocatalytic Stetter Cyclization of Pentoses for the Synthesis of Polyhydroxylated Cyclopentanone Scaffolds.

ABSTRACT: An organocatalytic approach for the carbocyclization of aldopentoses is disclosed. After initial activation, with the introduction of the intramolecular Michael acceptor in the substrate, the NHC-catalyzed Stetter reaction can be performed, giving rise to cyclopentanone scaffolds bearing multiple chiral centers and protected hydroxy groups. An optional controlled one-pot elimination provides the corresponding cyclopentenones as well. Due to the commercial availability of d- and l-pentoses all possible stereochemical permutations of the products can be prepared conveniently and affordably.

SUBMITTER: Suster C 

PROVIDER: S-EPMC12519462 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature