Simple and Versatile Scheme for the Stereochemical Identification of Natural Products and Diverse Organic Compounds with Multiple Asymmetric Centers

Semenov, Valentin A.; Krivdin, Leonid B.

doi:10.1021/acs.jpca.1c08687

Cited by 9 publications

(14 citation statements)

References 37 publications

(76 reference statements)

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“…Very recently, Semenov and Krivdin [ 362 ] proposed a simple and versatile scheme of the stereochemical identification of the stereochemically rich natural products and organic compounds with multiple asymmetric centers, as presented in an illustrative way in Scheme 14. This computational scheme is based on the calculation of 1 H and 13 C NMR chemical shifts in combination with their DP4+ analysis, as was exemplified in the original publication [ 362 ] with three natural products with multiple asymmetric centers including, in particular, sungucine ( 80 ) very well‐known for its activity against leukemia cells, which is shown in Figure 36.…”

Section: Computational 1h and 13c Nmr In Stereochemical Studies Of In...mentioning

confidence: 99%

“…Asymmetric centers are given in green. Reproduced with minor editing privilege from Semenov and Krivdin [362] with the permission of the American Chemical Society strychnine and a previously unreported trachylobane diterpene natural product. [363] In that study, Buevich, et al.…”

Section: S C H E M E 1mentioning

confidence: 99%

“…The scheme of the stereochemical identification of the stereochemically rich natural products and organic compounds with multiple asymmetric centers. Reproduced from Semenov and Krivdin [362] with the permission of the American Chemical Society F I G U R E 3 6 Atom numbering and stereochemical structure of sungucine, optimized at the M06-2X/aug-cc-pVQZ level. Asymmetric centers are given in green.…”

Section: S C H E M E 1mentioning

confidence: 99%

Section: Computational 1h and 13c Nmr In Stereochemical Studies Of In...mentioning

confidence: 99%

“…Asymmetric centers are given in green. Reproduced with minor editing privilege from Semenov and Krivdin [ 362 ] with the permission of the American Chemical Society…”

Section: Computational 1h and 13c Nmr In Stereochemical Studies Of In...mentioning

confidence: 99%

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Computational¹H and¹³C NMR in structural and stereochemical studies

Krivdin

2022

Magnetic Reson in Chemistry

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Present review outlines the advances and perspectives of computational 1H and 13C NMR applied to the stereochemical studies of inorganic, organic, and bioorganic compounds, involving in particular natural products, carbohydrates, and carbonium ions. The first part of the review briefly outlines theoretical background of the modern computational methods applied to the calculation of chemical shifts and spin–spin coupling constants at the DFT and the non‐empirical levels. The second part of the review deals with the achievements of the computational 1H and 13C NMR in the stereochemical investigation of a variety of inorganic, organic, and bioorganic compounds, providing in an abridged form the material partly discussed by the author in a series of parent reviews. Major attention is focused herewith on the publications of the recent years, which were not reviewed elsewhere.

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Section: Computational 1h and 13c Nmr In Stereochemical Studies Of In...mentioning

confidence: 99%

Section: S C H E M E 1mentioning

confidence: 99%

Section: S C H E M E 1mentioning

confidence: 99%

Section: Computational 1h and 13c Nmr In Stereochemical Studies Of In...mentioning

confidence: 99%

“…Asymmetric centers are given in green. Reproduced with minor editing privilege from Semenov and Krivdin [ 362 ] with the permission of the American Chemical Society…”

Section: Computational 1h and 13c Nmr In Stereochemical Studies Of In...mentioning

confidence: 99%

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Computational¹H and¹³C NMR in structural and stereochemical studies

Krivdin

2022

Magnetic Reson in Chemistry

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Stereochemical and NMR computational study of some natural dimeric bisindole alkaloids

Grigoriev,

Semenov,

Angenot

et al. 2024

Int J of Quantum Chemistry

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The initial conformational search followed by the optimization of geometric parameters and high‐level calculation of 1H and 13C NMR chemical shifts were carried out for 12 bisindole alkaloids of the Corynanthe‐Strychnos series. Configurational assignments of all compounds from this series were performed based on the correlation of calculated and experimental NMR chemical shifts. For some alkaloids, the reassignment of the individual resonances together with spectral assignment of experimentally unresolved signals were suggested.

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Configurational and Conformational Studies of Quinolizidine and Beta‐Carboline Moieties in the Corynanthe‐Tryptamine Alkaloids

Grigoriev,

Semenov,

Angenot

et al. 2024

Int J of Quantum Chemistry

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Configurational and conformational assignments of 11 Corynanthe‐Tryptamine alkaloids (usambarane skeleton) were performed based on the correlation of the high‐level calculated and experimental 1H and 13C NMR chemical shifts. For some compounds, the reassignment of a number of individual signals together with spectral assignment of experimentally unresolved peaks was suggested. The different conformations of the C/D quinolizidine ring system appear strictly dependent of the structure of the side chain (ethyl‐, vinyl‐ or ethylidenic); in the latter case, the configuration (E or Z) of the 19‐20 double bond of the ethylidenic chain is determinant to establish a cis‐ or a trans‐quinolizidine system of rings C/D. The conformation is also influenced by the equatorial or axial conformation of (C15) substituents.

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Simple and Versatile Scheme for the Stereochemical Identification of Natural Products and Diverse Organic Compounds with Multiple Asymmetric Centers

Cited by 9 publications

References 37 publications

Computational¹H and¹³C NMR in structural and stereochemical studies

Computational¹H and¹³C NMR in structural and stereochemical studies

Stereochemical and NMR computational study of some natural dimeric bisindole alkaloids

Configurational and Conformational Studies of Quinolizidine and Beta‐Carboline Moieties in the Corynanthe‐Tryptamine Alkaloids

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Simple and Versatile Scheme for the Stereochemical Identification of Natural Products and Diverse Organic Compounds with Multiple Asymmetric Centers

Cited by 9 publications

References 37 publications

Computational1H and13C NMR in structural and stereochemical studies

Computational1H and13C NMR in structural and stereochemical studies

Stereochemical and NMR computational study of some natural dimeric bisindole alkaloids

Configurational and Conformational Studies of Quinolizidine and Beta‐Carboline Moieties in the Corynanthe‐Tryptamine Alkaloids

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Computational¹H and¹³C NMR in structural and stereochemical studies

Computational¹H and¹³C NMR in structural and stereochemical studies