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Synthesis of the Cyanobacterial Antibiotics Anaephenes A and B

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journal contribution
posted on 26.05.2020, 20:14 by David L. Kukla, Juan Canchola, Jonathan J. Mills
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.