Determination of the Absolute Configuration of Two Pairs of C-8 − C-9′ Linked Neolignan Enantiomers

• Published in: Chirality (New York, N.Y.) Vol. 26; no. 12; pp. 825 - 828
• Main Authors: Bao, Jing-Mei, Cheng, Zhong-Bin, Zhang, Jun-Sheng, Zhu, Jian-Yong, Tang, Gui-Hua, Gan, Li-She, Yin, Sheng
• Format: Journal Article
• Language: English
• Published: HOBOKEN Blackwell Publishing Ltd 01.12.2014; Wiley; Wiley Subscription Services, Inc
• Subjects: absolute configuration; C-8 − C-9′ linked skeleton; Chemistry; Chemistry, Analytical; Chemistry, Medicinal; Chemistry, Organic; Chirality; Circular Dichroism; Density functional theory; DFT; ECD; Enantiomers; Life Sciences & Biomedicine; Lignans - chemistry; Magnetic Resonance Spectroscopy; Mathematical analysis; Molecular Conformation; Molecular Structure; neolignan enantiomers; Pharmacology & Pharmacy; Physical Sciences; Plant Leaves - chemistry; Science & Technology; Spectra; Stereoisomerism; Taxaceae - chemistry; Torreya yunnanensis; neolignan enantiomers; DFT; absolute configuration; Torreya yunnanensis; C-8-C-9 linked skeleton; ECD; C-8 − C-9′ linked skeleton
• ISSN: 0899-0042; 1520-636X; 1520-636X
• DOI: 10.1002/chir.22395

ABSTRACT Two pairs of new neolignan enantiomers, (±)‐torreyayunan A (1a/1b) and (±)‐torreyayunan B (2a/2b), featuring a rare C‐8 − C‐9′ linked skeleton, were isolated from leaves and twigs of Torreya yunnanensis. Their absolute configuration involving two chiral centers was determined by combined spectral and Density Functional Theory (DFT) calculation. This is the first report of the absolute configuration of this group of neolignans. Chirality 26:825–828, 2014. © 2014 Wiley Periodicals, Inc.