Syntheses of the terpenoid precursors cyclopent-2-enone and cyclohex-2-enone diesters

I. Kádas, V. Morvai, G. Árvai, L. Toke, A. Szöllosy, G. Tóth, M. Bihari

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7 Citations (Scopus)

Abstract

Two reaction pathways were elaborated for the practical and convenient synthesis of the title compounds. The first route applies a bromination-dehydrobromination sequence to introduce the double bond into 1-alkoxycarbonyl-2-oxocycloalkylacetic and propionic esters (4a-c, 7a, b). The application of 2,6-lutidine for dehydrobromination of α-bromocycloalkanones diesters (5a-c, 8a, b) provides sufficient selectivity to carry out this step without affecting the sensitive ester group. Alternative pathways, involving Michael reaction of diethyl 2-acetylsuccinate or -glutarate with acrolein and subsequent intramolecular aldol condensation, are presented in the case of cyclohex-2-enone derivatives 2a, b.

Original languageEnglish
Pages (from-to)107-117
Number of pages11
JournalMonatshefte für Chemie Chemical Monthly
Volume126
Issue number1
DOIs
Publication statusPublished - Jan 1 1995

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Keywords

  • 2,6-Lutidine
  • Aldol condensation
  • Bromination
  • Cyclopent-2-enone and cyclohex-2-enone derivatives
  • Dehydrobromination

ASJC Scopus subject areas

  • Chemistry(all)

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