Stereochemistry of atropisomeric 9,10-dihydrophenanthrene dimers from Pholidota chinensis

Sheng Yao, Chun Ping Tang, Yang Ye, T. Kurtán, Attila Kiss-Szikszai, S. Antus, Gennaro Pescitelli, Piero Salvadori, Karsten Krohn

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Nine bis-9,10-dihydrophenanthrene and 9,10-dihydrophenanthrene/(dihydro)stilbene derivatives, including the new phochinenins G-L 1-6, were isolated from the whole plant of Pholidota chinensis. Their structures were elucidated on the basis of extensive spectroscopic investigations (1D, 2D NMR, and HR-EIMS). Owing to the sterically hindered rotation around the biaryl axis, some of these biaryl compounds can exist as a pair of enantiomers, but were isolated as racemates. Computed inversion barriers of selected atropisomeric derivatives suggested that phochinenins K 5, gymconpin C 7, and flavanthrin 9 have stable atropisomers. Their racemates were separated by HPLC on an optically active stationary phase, and were stereochemically characterized on-line by circular dichroism (CD) spectroscopy (LC-CD coupling), in conjunction with quantum-mechanics CD calculations.

Original languageEnglish
Pages (from-to)2007-2014
Number of pages8
JournalTetrahedron Asymmetry
Volume19
Issue number17
DOIs
Publication statusPublished - Sep 8 2008

Fingerprint

Stereochemistry
stereochemistry
Dichroism
Circular Dichroism
Dimers
dichroism
dimers
Circular dichroism spectroscopy
Derivatives
Stilbenes
Enantiomers
Quantum theory
stilbene
enantiomers
Nuclear magnetic resonance
Mechanics
quantum mechanics
Spectrum Analysis
High Pressure Liquid Chromatography
inversions

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Stereochemistry of atropisomeric 9,10-dihydrophenanthrene dimers from Pholidota chinensis. / Yao, Sheng; Tang, Chun Ping; Ye, Yang; Kurtán, T.; Kiss-Szikszai, Attila; Antus, S.; Pescitelli, Gennaro; Salvadori, Piero; Krohn, Karsten.

In: Tetrahedron Asymmetry, Vol. 19, No. 17, 08.09.2008, p. 2007-2014.

Research output: Contribution to journalArticle

Yao, S, Tang, CP, Ye, Y, Kurtán, T, Kiss-Szikszai, A, Antus, S, Pescitelli, G, Salvadori, P & Krohn, K 2008, 'Stereochemistry of atropisomeric 9,10-dihydrophenanthrene dimers from Pholidota chinensis', Tetrahedron Asymmetry, vol. 19, no. 17, pp. 2007-2014. https://doi.org/10.1016/j.tetasy.2008.08.013
Yao, Sheng ; Tang, Chun Ping ; Ye, Yang ; Kurtán, T. ; Kiss-Szikszai, Attila ; Antus, S. ; Pescitelli, Gennaro ; Salvadori, Piero ; Krohn, Karsten. / Stereochemistry of atropisomeric 9,10-dihydrophenanthrene dimers from Pholidota chinensis. In: Tetrahedron Asymmetry. 2008 ; Vol. 19, No. 17. pp. 2007-2014.
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