Synthesis of naturally occurring o-heterocyclic compounds of biological activity

Sándor Antus, Katalin Gulácsi, László Juhász, Loránd Kiss, Tibor Kurtán

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Abstract

The total synthesis of (-)-cabenegrin A-I was achived via (-)-6aR,11ar maackiain, which was obtained by optical resolution of racemic maackiain using S-(-)-α-methylbenzyl isocyanate. The synthesis of rac-maackiain was performed both with the Heck oxyarylation of 7-benzyloxy-2H-chromene and the BF3·OEt2 mediated ring closure of isoflavan-4-ol derivatives, the latter of which provided much higher yields. The first enantioselective synthesis of trans-6aS,11aR-pterocarpan and its conversion to cis-6aS,11aS-ptarocarpan was also presented starting from racemic 2′-benzyloxyflavanone. Their stereochemistry was deduced by circular dichroism (CD) as well as by X-ray analysis of the ketal intermediate.

Original languageEnglish
Pages (from-to)1025-1032
Number of pages8
JournalPure and Applied Chemistry
Volume76
Issue number5
DOIs
Publication statusPublished - May 2004

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ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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