Chiroptical properties and synthesis of enantiopure cis and trans pterocarpan skeleton

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35 Citations (Scopus)

Abstract

The first enantioselective synthesis of trans-(6aS, 11aR)-pterocarpan [(+)-2] and its conversion to cis-(6aS, 11aS)-pterocarpan [(+)-1] was achieved starting from racemic 2′-benzyloxyflavanone (rac-3). Their stereochemistry was deduced by X-ray analysis of the ketal intermediate (-)-5a. The CD study of (+)-1 and (+)-2 allows the configurational assignment of similar pterocarpan derivatives by CD spectroscopy.

Original languageEnglish
Pages (from-to)558-563
Number of pages6
JournalChirality
Volume15
Issue number6
DOIs
Publication statusPublished - Jun 30 2003

Keywords

  • 2,3-dihydrobenzo [b]furan
  • Asymmetric synthesis
  • Chromane
  • Configurational assignment
  • Helicity rule

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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