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

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University Institute of Bio-Organic Chemistry "Antonio González", Center for Biomedical Research of the Canary Islands (CIBICAN), University of La Laguna, Astrofísico Francisco Sánchez 2, La Laguna 38206, Tenerife, Spain
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Department of Chemistry, Chemistry Institute, Sciences Faculty, Autonomous University of Santo Domingo, University City, Santo Domingo 1355, Dominican Republic
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Department of Chemical Engineering and Pharmaceutical Technology, University of La Laguna, La Laguna 38206, Tenerife, Spain
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Department of Organic Chemistry, University of La Laguna, La Laguna 38206, Tenerife, Spain
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2014, 12(7), 4031-4044; https://doi.org/10.3390/md12074031
Received: 25 February 2014 / Revised: 28 March 2014 / Accepted: 10 April 2014 / Published: 1 July 2014
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 (14) 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. View Full-Text
Keywords: C15 tetrahydrofuranyl-acetogenins; marilzafurollenes; marine natural products; Laurencia; five-membered rings; J-based methodologies; DFT calculations C15 tetrahydrofuranyl-acetogenins; marilzafurollenes; marine natural products; Laurencia; five-membered rings; J-based methodologies; DFT calculations
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Gutiérrez-Cepeda, A.; Daranas, A.H.; Fernández, J.J.; Norte, M.; Souto, M.L. Stereochemical Determination of Five-Membered Cyclic Ether Acetogenins Using a Spin-Spin Coupling Constant Approach and DFT Calculations. Mar. Drugs 2014, 12, 4031-4044.

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