2021
DOI: 10.1177/1934578x21996166
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Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Abstract: 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 c… Show more

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Cited by 15 publications
(40 citation statements)
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References 146 publications
(248 reference statements)
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“…Two NMR criteria for the C-22/C-23 AC assignment were already proposed. The first criterion 10 was based on a qualitative conformational analysis of a series of sterols, including 13 and 14, which considered the 13 C NMR chemical shift for C-22 and C-23 in the 22R,23R stereoisomers is very similar, showing a Δδ around 0.1 ppm. Whereas in the 22S,23S series this Δδ is around 4.6 ppm.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Two NMR criteria for the C-22/C-23 AC assignment were already proposed. The first criterion 10 was based on a qualitative conformational analysis of a series of sterols, including 13 and 14, which considered the 13 C NMR chemical shift for C-22 and C-23 in the 22R,23R stereoisomers is very similar, showing a Δδ around 0.1 ppm. Whereas in the 22S,23S series this Δδ is around 4.6 ppm.…”
Section: Resultsmentioning
confidence: 99%
“…The most stable DFT B3LYP/DGDZVP conformers of (5R,6S,22S,23S)-diepoxystigmasteryl acetate ( 22) T A B L E 5 NMR data of 3, 12-14 (in CDCl 3 , 1 H 500 at MHz, 13 C 125 at MHz)…”
Section: 62223-diepoxystigmasteryl Acetates 19-22mentioning
confidence: 99%
“…In addition, naturally occurring benzodihydrofurans 1 and 2 were successfully tested 4 as growth inhibitors of the insect species Tenebrio molitor, while the structure of 1 was independently verified 5 in a single-crystal x-ray diffraction (XRD) study. 5 From our three lustrous vibrational circular dichroism (VCD) experience, accumulated since the first study 6 of alkaloids from plants of Chilean origin, through the years during which a few VCD reviews 7,8 were put forward, 9 until current times, 10 it could be expected that the structural attributes of 1 would allow a straightforward AC determination of the molecule. Inspection of the structure of 1 reveals that this C 22 H 20 O 5 compound possesses only 4 sp 3 carbon atoms of which one is a methyl group, a sole stereogenic center which is located at C-2 on a benzodihydrofuran ring system and has an almost rigid p-hydroxycinnamoyl ester group whose phenolic hydroxy group can adopt 2 orientations.…”
Section: Introductionmentioning
confidence: 99%
“…Ambiguity from NMR arises often from the lack of configuration assignment to chiral structure elements, while planar structures are generally defined to a high level of accuracy [14]. While NMR spectra offer the possibility of distinguishing between diastereomers, even for compounds in mixtures, enantiomer identification requires either the isolation of pure compounds for their study by chiroptical methods or chemical derivatization by a homochiral reagent and subsequent NMR analysis [15,16].…”
Section: Introductionmentioning
confidence: 99%