Issue 25, 2012
From the journal:

Organic & Biomolecular Chemistry

Synthesis of the trans-hydrindane core of dictyoxetane†

Benedicte Defaut,a   Thomas B. Parsons,a   Neil Spencer,a   Louise Male,a   Benson M. Kariuki‡a  and  Richard S. Grainger*a  

* Corresponding authors

a School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK
E-mail: r.s.grainger@bham.ac.uk
Fax: +44 (0)1214144403
Tel: +44 (0)121 4144465

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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Article information

DOI
https://doi.org/10.1039/C2OB25384D
Article type
Paper
Submitted
22 Feb 2012
Accepted
26 Apr 2012
First published
21 May 2012

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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