Synfacts 2017; 13(12): 1225
DOI: 10.1055/s-0036-1591634
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Actinophyllic Acid

Erick M. Carreira
Matthieu J. R. Richter
Yoshii Y. Tokuyama H. Chen DY.-K. * Seoul National University, Republic of Korea and Tohoku University, Sendai, Japan
Total Synthesis of Actinophyllic Acid.

Angew. Chem. Int. Ed. 2017;
56: 12277-12281
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17. November 2017 (online)



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.