Synthesis of (±)-Actinophyllic Acid

doi:10.1055/s-0028-1087293

Synfacts 2008(12): 1241-1241
DOI: 10.1055/s-0028-1087293

Synthesis of Natural Products and Potential Drugs

Synthesis of (±)-Actinophyllic Acid

Rezensent(en):Philip Kocienski, Stewart Eccles

C. 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

Abstract

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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.

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