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Synfacts 2008(12): 1241-1241
DOI: 10.1055/s-0028-1087293
DOI: 10.1055/s-0028-1087293
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (±)-Actinophyllic Acid
Contributor(s):Philip Kocienski, Stewart EcclesC. L. Martin, L. E. Overman*, J. M. Rohde
University of California, Irvine, USA
Total Synthesis of (±)-Actinophyllic Acid
J. Am. Chem. Soc. 2008, 130: 7568-7569
University of California, Irvine, USA
Total Synthesis of (±)-Actinophyllic Acid
J. Am. Chem. Soc. 2008, 130: 7568-7569
Further Information
Publication History
Publication Date:
20 November 2008 (online)
Key words
actinophyllic acid - aza-Cope rearrangement - Mannich reaction - oxidative enolate coupling
Significance
()-Actinophyllic acid was isolated from the leaves of the tree Alstonia actinophylla. It is an inhibitor of carboxypeptidase U, an endogenous inhibitor of the process the body uses to clear fibrin clots. This synthesis proceeds in only eight stages all but one of which construct C-C or C-N bonds.
Comment
The oxidative coupling (C → D) of the piperidinone and malonate enolates by an iron(III) oxidant is believed to be the first intramolecular example. The bulky tert-butyl ester groups blocked one face of the ketone towards nucleophilic attack (D → E) resulting in a single isomer.