Chiroptical study and absolute configuration of securinine oxidation products

Natural Product Research
Egor ChirkinFrançois-Hugues Porée

Abstract

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.

References

May 28, 2009·Natural Product Reports·Steven M Weinreb
Aug 28, 2009·Journal of Natural Products·Nadja CachetOlivier P Thomas
Nov 22, 2012·Angewandte Chemie·Hao WeiChuang-chuang Li
Feb 3, 2015·Expert Opinion on Therapeutic Patents·Peng-Cheng Lv, Hai-Liang Zhu
Apr 8, 2015·The Alkaloids. Chemistry and Biology·Eqor ChirkinFrançois-Hugues Porée

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Methods Mentioned

BETA
circular dichroism
NMR
X-ray
electronic dichroism

Software Mentioned

SpecDis
Gaussian09
ORTEP
TDDFT

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