Molecules
Molecules
5 years ago

Stereopermutation on the Putative Structure of the Marine Natural Product Mucosin.

Antonsen, Nolsøe, Gallantree-Smith, Hansen, Görbitz, Stenstrøm
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*.

Publisher URL: http://doi.org/10.3390/molecules22101720

DOI: 10.3390/molecules22101720

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