Journal
MARINE DRUGS
Volume 12, Issue 7, Pages 4031-4044Publisher
MDPI AG
DOI: 10.3390/md12074031
Keywords
C-15 tetrahydrofuranyl-acetogenins; marilzafurollenes; marine natural products; Laurencia; five-membered rings; J-based methodologies; DFT calculations
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Funding
- Ministry of Economy and Competitiveness of Spain [SAF2011-28883-C03-01]
- EU [FP7-KBBE-3-245137, FP7-REGPOT-2012-CT2012-316137]
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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 C-15 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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