Absolute configuration assignment of oxindole derivatives by vibrational circular dichroism exciton coupling

Bautista-Hernández, Claudia I.; Cordero-Rivera, Reyna E.; Zúñiga-Estrada, Erick A.; Trejo‐Carbajal, Nayely; Meléndez-Rodrı́guez, Myriam; Suárez‐Castillo, Oscar R.; Sánchez-Zavala, Maricruz; Morales‐Ríos, Martha S.; Joseph‐Nathan, Pedro

doi:10.1016/j.tetasy.2016.06.004

Cited by 8 publications

(4 citation statements)

References 32 publications

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“…130 Similar studies of indolyl derivatives were developed for the AC assignment of secondary alcohols in the ester series 131 and primary amines in the amide series. 132…”

Section: Resultsmentioning

confidence: 99%

“…Exceptions to such calculations are those limited cases for which VCDEC was employed. 33,40,73,74,88,91,112,130 -132 A relevant aspect of the calculation task is the selection of the level of theory that has to be used to provide a good spectra comparison and consequently a confident AC assignment, which implies balancing spectra similarity and invested computer resources for the calculations. This situation is not very relevant when a single stereogenic center is present in the molecule under study since the AC is correctly defined in most cases, although with different levels of confidence.…”

Section: Resultsmentioning

confidence: 99%

“…130 Similar studies of indolyl derivatives were developed for the AC assignment of secondary alcohols in the ester series 131 and primary amines in the amide series. 132 The AC of a levorotatory alkaloid, found in Galanthus woronowii and G. nivalis, was established using several solution-state techniques like NMR, VCD, and ROA as (−)-(4aS, 6R,8aS)-galantamine (274) (Figure 78). 133 The IR and VCD spectra of matrine (275), sophoridine (276), oxymatrine (277), artemisinin (278), and dihydroartemisinin (279) ( Figure 79) were measured in CDCl 3 and DMSO-d 6 solutions to get their stereochemical information, including AC and conformational behavior.…”

Section: Nitrogenated Compoundsmentioning

confidence: 99%

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Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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Although demonstrated in 1975, vibrational circular dichroism (VCD) finally started to popularize during this century as a reliable tool to determine the absolute configuration (AC) of organic molecules. This research field continues to be a very dynamic one, in particular for the study of natural products which are a unlimited source of chiral molecules. It therefore turns of interest to summarize the accomplishments published in recent years and to comment on some eventual difficulties that emerged in rare cases to complete the AC determination task. Therefore the aim of this review is to update VCD results for the AC assignment of natural products published from 2015 to 2019, a period in which VCD was reported in some 126 publications involving almost 300 molecules. They are organized according the type of studied metabolite allowing an easily search. The molecules correspond to 28 monoterpenes concerning 17 papers, to 42 sesquiterpenes in 14 papers, to 51 diterpenes in 19 publications, to 5 other terpenoids in three papers, to 48 aromatic molecules in 15 reports, to 20 polyketides in 10 publications, to 27 miscellaneous formulas also in 10 papers, and to 76 nitrogen containing compounds, which include alkaloids and their synthetic analogs, in 38 articles. The landscape of reviewed molecules is quite wide as it goes from simple monoterpenes, like borneol or camphor, to very relevant biological molecules like the alkaloid cocaine or tadalafil samples to distinguish genuine and counterfeit Cialis®. In addition, 5 natural products and a simple derivative published outside the reviewed period, were used to illustrate some aspects of density functional theory calculations.

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“…130 Similar studies of indolyl derivatives were developed for the AC assignment of secondary alcohols in the ester series 131 and primary amines in the amide series. 132…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Nitrogenated Compoundsmentioning

confidence: 99%

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Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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“…17,18 On the basis of this correlation, structures of various molecules have been analysed with or without introduction of extra carbonyl chromophores, in a similar manner to the applications of the ECD exciton chirality method. [19][20][21][22][23][24][25][26][27][28][29][30] VCD couplet is also used for signal augmentation that leads to VCD measurements with reduced sample amount and with a short acquisition time. For example, VCD couplet of 1 was observed even at a concentration of 2.5 mM.…”

Section: Introductionmentioning

confidence: 99%

Exploration of chromophores for a VCD couplet in a spectrally transparent infrared region for biomolecules

Taniguchi

Zubir

Harada

et al. 2021

Phys. Chem. Chem. Phys.

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2018

Differentiation of Chiral Compounds Using NMR Spectroscopy

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Absolute configuration assignment of oxindole derivatives by vibrational circular dichroism exciton coupling

Cited by 8 publications

References 32 publications

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Exploration of chromophores for a VCD couplet in a spectrally transparent infrared region for biomolecules

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