Enantioselective Synthesis of Gamma-Butenolides from Streptomyces rochei and Derivatives

Given the challenges of discovering new natural products, further investigations into the regulatory systems that control their production are needed. Herein, we describe an enantioselective, divergent synthesis of two known autoregulators from Streptmyces rochei, the Streptomyces rochei butenolides (SRBs), along with nine derivatives. Key reactions include enantioselective alkynylation and regioselective photo-oxidation We also develop a quantitative green-fluorescence protein (GFP) based reporter assay and use this assay to assess key structural features for natural product induction.