Synthesis of the trans-hydrindane core of dictyoxetane

Benedicte Defaut; Thomas B. Parsons; Neil Spencer; Louise Male; Benson M. Kariuki; Richard S. Grainger

doi:10.1039/c2ob25384d

Synthesis of the trans-hydrindane core of dictyoxetane

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

Chemistry

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4926-4932
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	25
Early online date	21 May 2012
DOIs	https://doi.org/10.1039/c2ob25384d
Publication status	Published - 7 Jul 2012

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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AU - Defaut, Benedicte

AU - Parsons, Thomas B.

AU - Spencer, Neil

AU - Male, Louise

AU - Kariuki, Benson M.

AU - Grainger, Richard S.

PY - 2012/7/7

Y1 - 2012/7/7

N2 - 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.

AB - 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.

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ER -

Synthesis of the trans-hydrindane core of dictyoxetane

Abstract

ASJC Scopus subject areas

UN SDGs

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