stereochemical determination of five-membered cyclic ether acetogenins using a spin-spin coupling constant approach and dft calculations

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ID: 246056
2014
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Abstract
Five-membered rings are of particular interest, due to their presence in some of the most common molecules in chemistry and biology. Despite their apparent simplicity, the structural resolution of these rings is complex, due to their inherent conformational flexibility. Here, we describe an application of a recently reported simple and efficient NMR protocol based on the measurement of spin-spin coupling constants to achieve the challenging relative configurations of five new halogenated C15 tetrahydrofuranyl-acetogenins, marilzafurollenes A–D (1–4) and 12-acetoxy-marilzafurenyne (5), isolated from the red alga, Laurencia marilzae. Although DFT chemical shift calculations were used to connect remote stereocenters, the NMR-based approach seems advantageous over computational techniques in this context, as the presence of halogens may interfere with reliable calculations.
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gutirrez-cepeda2014marinestereochemical Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors ;Adrián Gutiérrez-Cepeda;Antonio Hernández Daranas;José J. Fernández;Manuel Norte;María L. Souto
Journal jixie gongcheng xuebao/journal of mechanical engineering
Year 2014
DOI
10.3390/md12074031
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