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

Making use of a Diels-Alder approach based on various alpha,beta-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 similar to 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.

Automated summary

Using a Diels-Alder approach with various alpha,beta-unsaturated 2-carbomethoxy-4,4-dimethyl-1-tetralones as dienophiles, polycyclic adducts were synthesized efficiently in yields ranging from 74% to 99% in the presence of Lewis acid (e.g., SnCl4). This establishes a synthetic platform for creating a focused library of aromatic polyketide-like compounds for screening potential natural and non-natural antimicrobial agents.