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Synthesis of the trans-hydrindane core of dictyoxetane

Defaut, Benedicte, Parsons, Thomas B., Spencer, Neil, Male, Louise, Kariuki, Benson and Grainger, Richard S. 2012. Synthesis of the trans-hydrindane core of dictyoxetane. Organic & Biomolecular Chemistry 10 (25) , pp. 4926-4932. 10.1039/c2ob25384d

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Last Modified: 04 Jun 2017 04:59
URI: http://orca-mwe.cf.ac.uk/id/eprint/47165

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