A Convenient Diels-Alder Approach toward Potential Polyketide-like Antibiotics Using α-Activated α,β-Unsaturated 4,4-Dimethyl-1-tetralones as Dienophiles

Molecules. 2023 Mar 17;28(6):2739. doi: 10.3390/molecules28062739.

Abstract

Making use of a Diels-Alder approach based on various α,β-unsaturated 2-carbomethoxy-4,4-dimethyl-1-tetralones as novel dienophiles, the corresponding polycyclic adducts could be efficiently synthesized in good to high yields (74~99%) in the presence of Lewis acid (e.g., SnCl4). Accordingly, a synthetically useful platform is established to provide a focused aromatic polyketide-like library for screening of potential natural and non-natural antimicrobial agents.

Keywords: Diels–Alder cycloaddition; Lewis acid; MRSA; VRSA; dienophile; polyketides.

MeSH terms

  • Anti-Bacterial Agents* / pharmacology
  • Gene Library
  • Molecular Structure
  • Stereoisomerism
  • Tetralones*

Substances

  • Anti-Bacterial Agents
  • Tetralones