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Issue 10, 2011
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Synthesis of the gymnodimine tetrahydrofuran core through a Ueno–Stork radical cyclization

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Abstract

A straightforward access to the C10–C20 skeleton of gymnodimine, incorporating a tetrahydrofuran fragment, is described. The elaboration of the THF moiety is based on a stereocontrolled Ueno–Stork cyclization. A Lewis-acid mediated allylation of the resulting acetal at C13 and a Horner–Wadsworth–Emmons olefination on the ketone at C17 complete the synthesis.

Graphical abstract: Synthesis of the gymnodimine tetrahydrofuran core through a Ueno–Stork radical cyclization

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Publication details

The article was received on 15 Feb 2011, accepted on 11 Mar 2011 and first published on 11 Mar 2011


Article type: Paper
DOI: 10.1039/C1OB05240C
Citation: Org. Biomol. Chem., 2011,9, 3726-3732
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    Synthesis of the gymnodimine tetrahydrofuran core through a Ueno–Stork radical cyclization

    S. Toumieux, R. Beniazza, V. Desvergnes, R. Aráoz, J. Molgó and Y. Landais, Org. Biomol. Chem., 2011, 9, 3726
    DOI: 10.1039/C1OB05240C

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