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Synthesis of Actinophyllic Acid
Total Synthesis of Actinophyllic Acid.
Angew. Chem. Int. Ed. 2017;
17 November 2017 (online)
Key wordsactinophyllic acid - indole alkaloids - desymmetrization - nitrile oxide cycloaddition - palladium catalysis - aminoarylation
Actinophyllic acid is a highly congested, polycyclic indole alkaloid found in Alstonia actinophylla. It is a potent inhibitor in the coupled enzyme assay TAFIa/hippuricase. Chen and co-workers report a 13-step total synthesis of the title compound based on a desymmetrization strategy.
Nitrile oxide cycloaddition with dibromooxime C under basic conditions gave isoxazoline D. Two more steps led to isoxazole E, which was subjected to a deprotection/palladium-catalyzed aminoarylation sequence. Indole synthesis followed by acetal formation completed the total synthesis of actinophyllic acid.