Synthesis of the Cyanobacterial Antibiotics Anaephenes A and B
David L Kukla1, Juan Canchola1, Jonathan J Mills1
1Department of Chemistry, Illinois State University, Campus Box 4160, Normal, Illinois 61790-4160, United States.
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.
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