Synthesis of the Cyanobacterial Antibiotics Anaephenes A and B
David L. Kukla, Juan Canchola, Jonathan J. Mills
Abstract
The first syntheses of the antibacterial natural products anaephenes A (1) and B (2) are reported. Both natural products were synthesized in five linear steps from commercially available tert-butyl(3-iodophenoxy)dimethylsilane. Key steps for the synthesis included a Sonogashira cross-coupling and a Julia-Kocienski olefination to selectively construct the E-alkene present in the natural products. This synthetic route allowed the identities and antimicrobial activities of anaephenes A (1) and B (2) to be confirmed. Additionally, these compounds displayed antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA) with MIC values of 16 and 8 μg/mL, respectively.
Topics & Concepts
AntimicrobialSonogashira couplingStaphylococcus aureusAlkeneAntibioticsMethicillin-resistant Staphylococcus aureusMicrobiologyStereochemistryChemistryAntibacterial agentBacteriaBiologyCombinatorial chemistryOrganic chemistryGeneticsCatalysisPalladiumMicrobial Natural Products and BiosynthesisMarine Sponges and Natural ProductsChemical synthesis and alkaloids