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 HREIMS). 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 (LCCD coupling), in conjunction with quantum-mechanics CD calculations.

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

PESCITELLI, GENNARO;SALVADORI, PIERO;
2008

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 HREIMS). 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 (LCCD coupling), in conjunction with quantum-mechanics CD calculations.
Yao, Sheng; TANG CHUNG, Ping; Ye, Yang; Kurtan, Tibor; KISS SZIKSZAI, Attila; Antus, Sandor; Pescitelli, Gennaro; Salvadori, Piero; Krohn, Karsten
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/205503
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