A general CD-method for the configurational assignment of erythro-8.4′-oxyneolign-8′-enes

Krisztina Kónya, Tibor Kurtán, Attila Kiss-Szikszai, László Juhász, Sándor Antus

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10 Citations (Scopus)

Abstract

Resolution of erythro-7-hydroxy-3′,5′-dimethoxy-3,4- methylenedioxy-8.4′-oxyneolign-8′-ene 1c was achieved by preparing the diastereomeric esters with (-)-(R)-α-methoxyphenylacetic acid. The correlation of its CD properties with the absolute configuration established a general CD method for the configurational assignment of erythro-8.4′- oxyneolignenes: positive Cotton effects of the two low-energy CD transitions derive from 7R,8S configuration while the negative ones from 7S,8R. This rule allows the configurational assignment of erythro-8.4′-oxyneolignenes with different aromatic substitution pattern by a CD measurement.

Original languageEnglish
Pages (from-to)72-78
Number of pages7
JournalArkivoc
Volume2004
Issue number13
Publication statusPublished - Nov 25 2004

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Keywords

  • 8.4′-Oxyneolign-8′-enes
  • Absolute configuration
  • Circular dichroism
  • Mosher's method

ASJC Scopus subject areas

  • Organic Chemistry

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