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Synfacts 2010(7): 0737-0737  
DOI: 10.1055/s-0029-1220106
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (±)-Aspercyclide A

Contributor(s): Steven V. Ley, Kimberley A. Roper
J. L. Carr, D. A. Offermann, M. D. Holdom, P. Dusart, A. J. P. White, A. J. Beavil, R. J. Leatherbarrow, S. D. Lindell, B. J. Sutton, A. C. Spivey*
BayerCropScience AG, Frankfurt am Main, Germany; Imperial College, London and Guy"s Hospital Campus, London, UK
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Publication History

Publication Date:
22 June 2010 (online)

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Significance

Aspercyclide A is one of three ­fungal metabolites to be isolated from Aspergillus sp. found in soil extracts in 2004 and has been shown to have micromolar potency as a small molecule antagonist for blocking a protein-protein interaction that triggers an inflammatory mediator release. (+)-Aspercyclide C has been previously ­synthesized using a ring-closing metathesis to ­effect macrocyclization (A. Fürstner, C. Müller Chem. Commun. 2005, 5583). Recently, (+)-asper-cyclides A and B have also been synthesized ­using a Nozaki-Hiyama-Kishi reaction to effect macrocyclization (J. Pospíšil et al. Chem. Eur. J. 2009, 15, 5956).