Application of a Samarium(II)-Mediated Spirocyclisation in an Asymmetric Approach to the Cyclopentanol Motif of Stolonidiol

doi:10.1055/s-2007-1000821

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Synlett 2007(20): 3155-3159
DOI: 10.1055/s-2007-1000821

LETTER

Application of a Samarium(II)-Mediated Spirocyclisation in an Asymmetric Approach to the Cyclopentanol Motif of Stolonidiol

Lisa A. Sloan^a, Thomas M. Baker^a, Simon J. F. Macdonald^b, David J. Procter*^a
^a The School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK
^b GlaxoSmithKline R&D Ltd, Medicines Research Centre, Gunnels Wood Road, Stevenage, SG1 2NY, UK
Fax: +44(161)2754939; e-Mail: david.j.procter@manchester.ac.uk;

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Publication History

Received 21 August 2007
Publication Date:
03 December 2007 (eFirst)

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Abstract

An asymmetric approach to the cyclopentanol motif of the biologically active, marine natural product stolonidiol has been developed. The approach involves the asymmetric synthesis of chiral γ,δ-unsaturated ketones and their spirocyclisation using SmI₂.

Key words

samarium - radical reactions - asymmetric synthesis - natural products - spiro compounds