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Molecules 2017, 22(10), 1720; doi:10.3390/molecules22101720

Stereopermutation on the Putative Structure of the Marine Natural Product Mucosin

1
Faculty of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, 1433 Ås, Norway
2
Department of Chemistry, University of Oslo, P.O. Box 1033, 0315 Oslo, Norway
3
Department of Pharmaceutical Chemistry, University of Oslo, P.O. Box 1068, 0316 Oslo, Norway
Dedication: Dedicated to Lars Skattebøl on the occasion of his 90th birthday.
*
Author to whom correspondence should be addressed.
Received: 19 September 2017 / Revised: 3 October 2017 / Accepted: 5 October 2017 / Published: 13 October 2017
(This article belongs to the Section Natural Products)
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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*. View Full-Text
Keywords: marine hydrindane natural product; asymmetric synthesis; stereodivergent strategy; structural elucidation; eicosanoid marine hydrindane natural product; asymmetric synthesis; stereodivergent strategy; structural elucidation; eicosanoid
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MDPI and ACS Style

Antonsen, S.G.; Gallantree-Smith, H.; Görbitz, C.H.; Hansen, T.V.; Stenstrøm, Y.H.; Nolsøe, J.M.J. Stereopermutation on the Putative Structure of the Marine Natural Product Mucosin. Molecules 2017, 22, 1720.

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