Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 6, Issue 17, Pages 3085-3090Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b805951a
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- EPSRC
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In this paper we present results of a study into whether the tricyclic core of the lepadiformines A-C can be accessed via intramolecular hetero-Diels-Alder cycloaddition. We are able to demonstrate that such a process is possible and that the reaction proceeds in an endo-selective fashion, providing the correct relative stereochemistry for this family of natural products. By employing this approach we have been able to develop a short (7 step) synthesis of (+/-)-lepadiformine A. starting from commercially-available trans-2-nonenal.
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