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Stereochemical Determination of Five-Membered Cyclic Ether Acetogenins Using a Spin-Spin Coupling Constant Approach and DFT Calculations

AuthorsGutiérrez-Cepeda, Adrián; Hernández Daranas, Antonio ; Fernández, José J.; Norte, Manuel; Souto, María L.
KeywordsC15 tetrahydrofuranyl-acetogenins
Marine natural products
Five-membered rings
J-based methodologies
DFT calculations
Issue Date1-Jul-2014
PublisherMolecular Diversity Preservation International
CitationMarine Drugs 12(7): 4031-4044 (2014)
AbstractFive-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.
Publisher version (URL)https://doi.org/10.3390/md12074031
Appears in Collections:(IPNA) Artículos
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