Abstract
A stereodivergent total synthesis has been executed based on the plausibly misassigned structure of the unusual marine hydrindane mucosin (1). The topological connectivity of the four contiguous all-carbon stereocenters has been examined by selective permutation on the highlighted core. Thus, capitalizing on an unprecedented stereofacial preference of the cis-fused bicycle[4.3.0]non-3-ene system when a Michael acceptor motif is incorporated, copper-mediated conjugate addition furnished a single diastereomer. Cued by the relative relationship reported for the appendices in the natural product, the resulting anti-adduct was elaborated into a probative target structure 1*.
Highlights
Certain metabolites derived from polyunsaturated fatty acids (PUFAs) play a key role in mammalian physiology, where they orchestrate both inflammatory response as well as the return to homeostasis [1,2,3,4]
Using induced co-cyclisation as the pivotal feature, preliminary experimental work led them to conclude that thermodynamic control would favour the relative stereochemistry assigned et al [35]
By incorporating a Michael acceptor motif, we have revealed an innate topological bias of the cis-fused bicyclo[4.3.0]non-3-ene system
Summary
Certain metabolites derived from polyunsaturated fatty acids (PUFAs) play a key role in mammalian physiology, where they orchestrate both inflammatory response as well as the return to homeostasis [1,2,3,4]. Sea dwelling organisms have proven to be a abundant source of new chemical entities, set apart from those found in the terrestrial environment [24,25]. Mucosin (1) is a natural product that was isolated from the Mediterranean sponge. In NMR experiments on the isolated methyl ester, pertaining to both 1DMolecules 2017, 22, 1720; doi:10.3390/molecules22101720 www.mdpi.com/journal/molecules. In NMR experiments on the isolated methyl ester, terms of the four 1Dcontiguous stereocentres. NMR experiments on the isolated are methyl ester, pertaining to both and 2D-techniques, the In distinguishing resonances/correlations ensconced pertaining to aliphatic both 1Dand. The absence resonances/correlations ofare any coupling in pattern to in a crowded aliphatic region. On its own [35]
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