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Issue 25, 2012
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Synthesis of the trans-hydrindane core of dictyoxetane

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Abstract

A concise, stereoselective synthesis of the trans-hydrindane core of the marine natural product dictyoxetane is reported, starting from a Robinson annelation derived bicyclic enone. A phosphorane-mediated, pinacol-like rearrangement of a cis-diol, via a formal 1,2-hydride shift, is used to establish the requisite trans ring junction. 31P NMR supports the formation of the intermediate phosphorane, generated in situ from the reaction of a diol with Ph3PCl2.

Graphical abstract: Synthesis of the trans-hydrindane core of dictyoxetane

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Publication details

The article was received on 22 Feb 2012, accepted on 26 Apr 2012 and first published on 21 May 2012


Article type: Paper
DOI: 10.1039/C2OB25384D
Citation: Org. Biomol. Chem., 2012,10, 4926-4932
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    Synthesis of the trans-hydrindane core of dictyoxetane

    B. Defaut, T. B. Parsons, N. Spencer, L. Male, B. M. Kariuki and R. S. Grainger, Org. Biomol. Chem., 2012, 10, 4926
    DOI: 10.1039/C2OB25384D

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