Chiroptical study and absolute configuration of securinine oxidation products

被引：2

作者：

Chirkin, Egor ^{[1
]}

Atkatlian, William ^{[1
]}

Do, Quyen ^{[2
]}

Gaslonde, Thomas ^{[1
]}

Dufat, Thi-Hanh ^{[1
]}

Michel, Sylvie ^{[1
]}

Lemoine, Pascale ^{[3
,4
]}

Genta-Jouve, Gregory ^{[1
]}

Poree, Francois-Hugues ^{[1
]}

机构：

[1] Univ Paris 05, Lab Pharmacognosie UMR CNRS COMETE 8638, Fac Pharm, F-75006 Paris, France

[2] Hanoi Univ Pharm, Hanoi, Vietnam

[3] Univ Paris 05, Lab Cristallog, Fac Pharm, F-75006 Paris, France

[4] Univ Paris 05, RMN Biol UMR CNRS 8015, Fac Pharm, F-75006 Paris, France

来源：

NATURAL PRODUCT RESEARCH | 2015年 / 29卷 / 13期

关键词：

X-ray crystallography; TDDFT-ECD; securinine; absolute configuration; phyllanthidine; CIRCULAR-DICHROISM SPECTRA; ALKALOIDS; VIROALLOSECURININE; VIROSECURININE; PHYLLANTIDINE;

D O I：

10.1080/14786419.2015.1023727

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Time-dependant density functional theory-electronic circular dichroism spectra prediction was carried out to study the absolute configuration of phyllanthidine-type derivatives 5 and 6, derived from securinine (1) and its enantiomer virosecurinine (2), respectively. This method demonstrated to be very reliable in this alkaloid series. Thus, 5 and 6 shared the same stereochemistry as their parent precursors, confirming the retentive nature of the oxidation sequence. In addition, this study highlighted the key role of the methylene bridge (BC ring) in the chiroptical activity of these compounds. These results fully clarified the stereochemical relationships between the phyllanthidine and the securinine subgroups.

引用

页码：1235 / 1242

页数：8

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