Stereopermutation on the Putative Structure of the Marine Natural Product Mucosin

Simen G Antonsen; Harrison Gallantree-Smith; Carl Henrik Görbitz; Trond Vidar Hansen; Yngve H Stenstrøm; Jens M J Nolsøe

doi:10.3390/molecules22101720

Stereopermutation on the Putative Structure of the Marine Natural Product Mucosin

Molecules. 2017 Oct 13;22(10):1720. doi: 10.3390/molecules22101720.

Authors

Simen G Antonsen¹, Harrison Gallantree-Smith², Carl Henrik Görbitz³, Trond Vidar Hansen^{4

5}, Yngve H Stenstrøm⁶, Jens M J Nolsøe⁷

Affiliations

¹ Faculty of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, 1433 Ås, Norway. simen.antonsen@nmbu.no.
² Faculty of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, 1433 Ås, Norway. lithium_87@hotmail.co.uk.
³ Department of Chemistry, University of Oslo, P.O. Box 1033, 0315 Oslo, Norway. c.h.gorbitz@kjemi.uio.no.
⁴ Faculty of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, 1433 Ås, Norway. t.v.hansen@farmasi.uio.no.
⁵ Department of Pharmaceutical Chemistry, University of Oslo, P.O. Box 1068, 0316 Oslo, Norway. t.v.hansen@farmasi.uio.no.
⁶ Faculty of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, 1433 Ås, Norway. yngve.stenstrom@nmbu.no.
⁷ Faculty of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, 1433 Ås, Norway. jens.mj.nolsoe@nmbu.no.

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*.

Keywords: asymmetric synthesis; eicosanoid; marine hydrindane natural product; stereodivergent strategy; structural elucidation.

MeSH terms

Biological Products / chemistry*
Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Indans / chemistry*
Molecular Structure*
Stereoisomerism

Substances

Biological Products
Bridged Bicyclo Compounds, Heterocyclic
Indans
hydrindane
mucosin