Latent inhibitors part 11. The synthesis of 5-spirocyclopropyl dihydroorotic acid

Stephen Husbands, William Fraser, Colin J. Suckling, Hamish C S Wood

Research output: Contribution to journalArticle

Abstract

Approaches to the synthesis of 5-spirocyclopropyldihydroorotic acid are described. Difficulties were encountered in the lack of reactivity of diethyl 2-oxobutandicarboxylate and its derivatives towards cyclopropanation. Potential intermediates were prepared from ethyl 4-acetoxy-3-oxobutanoate but rearrangements involving ring expansion of the cyclopropane ring and hindrance towards condensation reactions of the ketone prevented formation of the pyrimidine. A successful route involving Strecker synthesis of a precursor aminoacid from ethyl 1-formyl-cyclopropane-1-carboxylate in which the formyl group was converted into the corresponding the urea led to the target compound.

Original languageEnglish
Pages (from-to)865-870
Number of pages6
JournalTetrahedron
Volume51
Issue number3
DOIs
Publication statusPublished - 16 Jan 1995

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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