Stereocontrolled access to δ-lactone-fused-γ-lactams bearing angular benzylic quaternary stereocenters.

ABSTRACT: C-fused γ-lactam-lactones are resident in several bioactive molecules, including anticancer agents such as omuralide. In this embodiment, we report mild conditions for the catalytic halolactonization of lactam-tethered 5-aryl-4(E)-pentenoic acids. The use of dichloromethane as the solvent and Ph₃P[double bond, length as m-dash]S as the catalyst led to predominant 6-endo-trig cyclization and furnished the trans-fused-γ-lactam-δ-lactones. The transformation is modular, regioselective, chemoselective, and diastereoselective. The γ-lactam-δ-lactones bear angular quaternary benzylic stereocenters, which is noteworthy since the presence of a quaternary carbon in bioactive small molecules often promotes an element of conformational restriction that imparts potency,

SUBMITTER: Beng TK 

PROVIDER: S-EPMC9194931 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature