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

Autor: Beng TK; Department of Chemistry, Central Washington University Ellensburg WA 98926 USA Timothy.beng@cwu.edu., Rodriguez MJ; Department of Chemistry, Central Washington University Ellensburg WA 98926 USA Timothy.beng@cwu.edu., Borg C; Department of Chemistry, Central Washington University Ellensburg WA 98926 USA Timothy.beng@cwu.edu.
Jazyk: angličtina
Zdroj: RSC advances [RSC Adv] 2022 Jun 14; Vol. 12 (27), pp. 17617-17620. Date of Electronic Publication: 2022 Jun 14 (Print Publication: 2022).
DOI: 10.1039/d2ra02167f
Abstrakt: 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 Ph 3 P[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, selectivity, and metabolic stability. The generated halogen and lactone motifs are important functional handles for late-stage diversification.
Competing Interests: There are no conflicts of interest to declare.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE
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