A new synthetic approach to the C‐D ring portion of streptonigrin analogues

John J. Kilama, Bhashyam S. Iyengar, William A. Remers, Eugene A. Mash

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

Development of an efficient synthesis of the C‐D ring portion of streptonigrin is a key operation in the synthesis of this antibiotic and its analogues. A new method for the synthesis of 3‐cyano‐5,6‐dimethyl‐4‐(3,4,5‐trimethoxyphenyl)‐2‐pyridone (14), a compound having the requisite functionality for conversion into a streptonigrin analogue, has been established. It involves treatment of 3,4,5‐trimethoxybenzonitrile with ethylmagnesium bromide and malononitrile to give propylenemalononitrile derivative 7, which is condensed with trimethyl orthoacetate to give a mixture of 9 and pyridine derivative 12. Demethylation of 12 then affords 14. The overall yield for this route was 50%, allowing for conversion of 9 to 12.

Original languageEnglish (US)
Pages (from-to)1437-1440
Number of pages4
JournalJournal of Heterocyclic Chemistry
Volume27
Issue number5
DOIs
StatePublished - Jan 1 1990

ASJC Scopus subject areas

  • Organic Chemistry

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