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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


IMPACT FACTOR 2017: 5.294

CiteScore 2017: 3.42

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1365-3075
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Volume 75, Issue 2-3

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Stereochemical analysis of natural products. Approaches relying on the combination of NMR spectroscopy and computational methods

R. Riccio
  • Corresponding author
  • Dipartimento di Scienze Farmaceutiche, Università di Salerno, via Ponte Don Melillo, 8408, Fisciano (SA), Italy
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/ Giuseppe Bifulco
  • Corresponding author
  • Dipartimento di Scienze Farmaceutiche, Università di Salerno, via Ponte Don Melillo, 8408, Fisciano (SA), Italy
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/ Paola Cimino
  • Corresponding author
  • Dipartimento di Scienze Farmaceutiche, Università di Salerno, via Ponte Don Melillo, 8408, Fisciano (SA), Italy
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/ Carla Bassarello
  • Corresponding author
  • Dipartimento di Scienze Farmaceutiche, Università di Salerno, via Ponte Don Melillo, 8408, Fisciano (SA), Italy
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/ Luigi Gomez-Paloma
  • Corresponding author
  • Dipartimento di Scienze Farmaceutiche, Università di Salerno, via Ponte Don Melillo, 8408, Fisciano (SA), Italy
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Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200375020295

The stereochemical study of flexible stereogenic carbon chains, such as those of many novel natural products, is a particularly challenging task. Recent applications of our group on the so-called "J-based approach", a methodology relying on a detailed analysis of homonuclear (H-H) and heteronuclear (C-H) 2,3J couplings, include the study of the sphinxolide family of antitumor macrolides, a group of molecules characterized by a flexible macrocyclic framework bearing a number of oxygenated and methylated undetermined stereocenters, and of ascaulitoxin, a nitrogen-containing phytotoxin with herbicidal activity produced by a phytopathogenic fungus. An extension of the original procedure, relying on a Hartree-Fock (HF) ab initio calculation of conformational equilibrium and an estimate of the Boltzmann averaged 2,3JHH and 2,3JCH couplings, has been applied to the stereochemical study of sapinofuranone A, where the conformational equilibrium among existing rotamers had initially led to controversial results. 13C NMR chemical shifts are additional useful parameters in the study of complex organic molecules. Along these lines, we have lately proposed the use of Hartree–Fock gauge including atomic orbitals (GIAO) calculated 13C NMR chemical shift values as a supporting tool for the validation of the structure of new natural products and the determination of the relative stereochemistry of diastereomeric flexible compounds that are characterized by multiple conformer equilibria.

Conference

IUPAC International Symposium on the Chemistry of Natural Products, International Symposium on the Chemistry of Natural Products, ISCNP, Natural Products, 23rd, Florence, Italy, 2002-07-28–2002-08-02

About the article

Published Online: 2009-01-01

Published in Print: 2003-01-01


Citation Information: Pure and Applied Chemistry, Volume 75, Issue 2-3, Pages 295–308, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200375020295.

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