New Synthesis and Some Selected Reactions of the Potential Ergot Alkaloid Precursor Indole-4-carboxaldehyde

Alan P. Kozikowski, Hitoshi Ishida, Yon Yih Chen

Research output: Contribution to journalArticlepeer-review

Abstract

As a consequence of the potential use of the ergot alkaloids and their derivatives in the treatment of Parkinson's disease and for the inhibition of prolactin release, we have been greatly interested in designing new strategies for the preparation of these products.2 Our retrosynthetic analysis of these compounds led us to consider routes based on the utilization of 4-C-substituted indoles as the key precursor molecules. Since no highly efficient procedures have been developed for the synthesis of such compounds, we initiated a study geared toward their production on a multigram scale.3 We would now like to disclose an excellent method for producing methyl indole-4-carboxylate (3) from the commercially available 3-nitro-2-methylbenzoic acid as well as to describe some reactions of this compound.

Original languageEnglish (US)
Pages (from-to)3350-3352
Number of pages3
JournalJournal of Organic Chemistry
Volume45
Issue number16
DOIs
StatePublished - Aug 1980

ASJC Scopus subject areas

  • Organic Chemistry

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