The synthesis of (-)-isodomoic acid C

Jonathan Clayden*, Faye E. Knowles, Ian R. Baldwin

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

73 Citations (Scopus)

Abstract

The neuroactive algal metabolite (-)-isodomoic acid C, a kainoid amino acid, has been synthesized for the first time. Asymmetric dearomatizing cyclization of an aromatic amide using a chiral lithium amide base generates a bicyclic enone containing a pyrrolidinone ring with the relative and absolute stereochemistry of the target. A further 15 synthetic steps, including conjugate cuprate addition to the enone of a side chain precursor, a Ru-promoted oxidation of the phenyl ring to the C2-carboxylic acid substituent, a regioselective Baeyer-Villiger reaction, and an E-selective Horner-Wadsworth-Emmons reaction, elaborate the cyclization product into the target molecule.

Original languageEnglish
Pages (from-to)2412-2413
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number8
Early online date5 Feb 2005
DOIs
Publication statusPublished - 2 Mar 2005

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