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Synthesis of the Marine Myxobacterial Antibiotic Enhygrolide A

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journal contribution
posted on 21.06.2017, 17:20 by Ramesh Muddala, Jaime A. M. Acosta, Luiz C. A. Barbosa, John Boukouvalas
The first synthesis of enhygrolide A, a scarce γ-alkylidenebutenolide antibiotic of the obligate marine myxobacterium Enhygromyxa salina, was achieved in five steps and 54% overall yield from tetronic acid. Key steps include (i) organocatalytic reductive alkylation, (ii) iron-catalyzed sp2–sp3 cross-coupling, and (iii) vinylogous aldol condensation. Aside from its brevity and reliance on environmentally sustainable processes, the synthesis demonstrates the serviceability of butenolide pivalates in cross-coupling reactions.