Actinophyllic acid is a complex indole alkaloid with an unprecedented hexacyclic structure that was isolated from Alstonia actinophylla in 2004. As a potent inhibitor of activated thrombin-activatable fibrinolysis inhibitor (TAFIa), it shows promise for the study of various aspects of thrombotic disease. A novel N-acyliminium ion mediated cascade reaction acts as the key construct in the synthesis, forming two new carbon-carbon bonds with remarkable efficiency. Intramolecular enolate alkylation, followed by global deprotection/hemiketalization completes the synthesis.

Total synthesis of ([plusmn])-actinophyllic acid

245th National Meeting (2013)

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