Assignment of the absolute configuration of zwitterionic and neutral macropodumines by means of TDDFT CD calculations

Yue Wei Guo, Tibor Kurtán, Karsten Krohn, Gennaro Pescitelli, Wen Zhang

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Macropodumines B and C (1, 2) are fused pentacyclic alkaloids previously isolated from the Chinese medicinal plant Daphniphyllum macropodum. Macropodumine B (1) possesses an amazing structural feature of a cyclopentadienyl carbanion, stabilized as a zwitterion by an internal iminium cation, which was confirmed by X-ray diffraction analysis. On the basis of the X-ray geometry, the absolute configuration of 1 was determined by employing the solid-state CD/TDDFT approach. The absolute configuration of 2 was instead determined by using TDDFT CD calculations on DFT-optimized geometries, in comparison with CD spectra recorded in solution.

Original languageEnglish
Pages (from-to)561-568
Number of pages8
JournalChirality
Volume21
Issue number6
DOIs
Publication statusPublished - Aug 13 2009

Keywords

  • Cyclopentadienyl carbanion
  • Daphniphyllum alkaloids
  • Solid-state CD/TDDFT approach
  • Solution vs. solid-state CD
  • X-ray diffraction analysis

ASJC Scopus subject areas

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

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