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Updated: Mar 5, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Macrophilone A: Structure Elucidation, Total Synthesis, and Functional Evaluation of a Biologically Active
Katherine Zlotkowski, William M Hewitt, Pengcheng Yan1
1School of Pharmaceutical Sciences, Wenzhou Medical University , Wenzhou, Zhejiang 325035, People's Republic of China.
Abstract:
A previously uncharacterized pyrroloiminoquinone natural product, macrophilone A, was isolated from the stinging hydroid Macrorhynchia philippina. The structure was assigned utilizing long-range NMR couplings and DFT calculations and proved by a concise, five-step total synthesis. Macrophilone A and a synthetic analogue displayed potent biological activity, including increased intracellular reactive oxygen species levels and submicromolar cytotoxicity toward lung adenocarcinoma cells.
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