Absolute configuration and total synthesis of (-)-cabenegrin A-I

Adrienne L. Tokés, György Litkei, Katalin Gulácsi, Sándor Antus, Eszter Baitz-Gács, Csaba Szántay, László L. Darkó

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30 Citations (Scopus)

Abstract

The total synthesis of (-)-cabenegrin A-I [(-)-1] in five steps was achieved from (-)-6aR, 11aR-maackiain [(-)-5], which in turn was prepared by the optical resolution of racemic (±)-5 using S-(-)α-methylbenzyl isocyanate as the the chiral auxiliary. The homochirality of(-)-maackiain [(- )-5] and (-)cabenegrin A-I [(-)-1] was proved by CD measurements. Synthesis of (±)maackiain [(±)-5] is also presented, starting from the readily available phenol derivatives resorcinol and sesamol, which demonstrates the synthetic utility of the Heck-type oxyarylation process for obtaining pterocarpane derivatives on a multigram scale. A new ring-opening reaction of pterocarpanes (7 → 28) is described.

Original languageEnglish
Pages (from-to)9283-9296
Number of pages14
JournalTetrahedron
Volume55
Issue number30
DOIs
Publication statusPublished - Jul 23 1999

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Keywords

  • Benzopyrans
  • Biologically active compounds
  • Flavanoids
  • Resolution

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Tokés, A. L., Litkei, G., Gulácsi, K., Antus, S., Baitz-Gács, E., Szántay, C., & Darkó, L. L. (1999). Absolute configuration and total synthesis of (-)-cabenegrin A-I. Tetrahedron, 55(30), 9283-9296. https://doi.org/10.1016/S0040-4020(99)00490-1