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Keywords = marine hydrindane natural product

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11 pages, 2920 KiB  
Concept Paper
Some Biogenetic Considerations Regarding the Marine Natural Product (−)-Mucosin
by Jens M. J. Nolsøe, Marius Aursnes, Yngve H. Stenstrøm and Trond V. Hansen
Molecules 2019, 24(22), 4147; https://doi.org/10.3390/molecules24224147 - 15 Nov 2019
Cited by 5 | Viewed by 4224
Abstract
Recently, the identity of the marine hydrindane natural product (−)-mucosin was revised to the trans-fused structure 6, thereby providing a biogenetic puzzle that remains to be solved. We are now disseminating some of our insights with regard to the possible machinery [...] Read more.
Recently, the identity of the marine hydrindane natural product (−)-mucosin was revised to the trans-fused structure 6, thereby providing a biogenetic puzzle that remains to be solved. We are now disseminating some of our insights with regard to the possible machinery delivering the established architecture. Aspects with regard to various modes of cyclization in terms of concerted versus stepwise processes are held up against the enzymatic apparatus known to be working on arachidonic acid (8). To provide a contrast to the tentative polyunsaturated fatty acid biogenesis, the structural pattern featured in (−)-mucosin (6) is compared to some marine hydrinane natural products of professed polyketide descent. Our appraisal points to a different origin and strengthens the hypothesis of a polyunsaturated fatty acids (PUFA) as the progenitor of (−)-mucosin (6). Full article
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18 pages, 2177 KiB  
Article
Stereopermutation on the Putative Structure of the Marine Natural Product Mucosin
by Simen G. Antonsen, Harrison Gallantree-Smith, Carl Henrik Görbitz, Trond Vidar Hansen, Yngve H. Stenstrøm and Jens M. J. Nolsøe
Molecules 2017, 22(10), 1720; https://doi.org/10.3390/molecules22101720 - 13 Oct 2017
Cited by 6 | Viewed by 5592
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, [...] Read more.
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*. Full article
(This article belongs to the Section Natural Products Chemistry)
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