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

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*.

SUBMITTER: Antonsen SG

PROVIDER: S-EPMC6151738 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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

Antonsen Simen G SG Gallantree-Smith Harrison H Görbitz Carl Henrik CH Hansen Trond Vidar TV Stenstrøm Yngve H YH Nolsøe Jens M J JMJ

Molecules (Basel, Switzerland) 20171013 10

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 additio ...[more]

PMID: 29027970

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