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

Yue Wei Guo, T. 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 - 2009

Fingerprint

Alkaloids
Geometry
Medicinal Plants
Discrete Fourier transforms
X-Ray Diffraction
X ray diffraction analysis
Cations
Positive ions
X-Rays
X rays
macropodumine B
isofenphos
macropodumine C

Keywords

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

ASJC Scopus subject areas

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

Cite this

Assignment of the absolute configuration of zwitterionic and neutral macropodumines by means of TDDFT CD calculations. / Guo, Yue Wei; Kurtán, T.; Krohn, Karsten; Pescitelli, Gennaro; Zhang, Wen.

In: Chirality, Vol. 21, No. 6, 2009, p. 561-568.

Research output: Contribution to journalArticle

Guo, Yue Wei ; Kurtán, T. ; Krohn, Karsten ; Pescitelli, Gennaro ; Zhang, Wen. / Assignment of the absolute configuration of zwitterionic and neutral macropodumines by means of TDDFT CD calculations. In: Chirality. 2009 ; Vol. 21, No. 6. pp. 561-568.
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