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Issue 19, 2011
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Synthesis of the C19 methyl ether of aspercyclide A viagermyl-Stille macrocyclisation and ELISA evaluation of both enantiomers following optical resolution

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Abstract

Aspercyclide A (1) is a biaryl ether containing 11-membered macrocyclic natural product antagonist of the human IgE-FcεRI protein-protein interaction (PPI); a key interaction in the signal transduction pathway for allergic disorders such as asthma. Herein we report a novel approach to the synthesis of the C19 methyl ether of aspercyclide A, employing a Pd(0)-catalysed, fluorous-tagged alkenylgermane/arylbromide macrocyclisation (germyl-Stille reaction) as the key step, and evaluation of both enantiomers of this compound via ELISA following optical resolution by CSP-HPLC. A crystal structure for germyl hydride 27 is also reported.

Graphical abstract: Synthesis of the C19 methyl ether of aspercyclide A viagermyl-Stille macrocyclisation and ELISA evaluation of both enantiomers following optical resolution

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Supplementary files

Article information


Submitted
31 May 2011
Accepted
04 Jul 2011
First published
08 Jul 2011

Org. Biomol. Chem., 2011,9, 6814-6824
Article type
Paper

Synthesis of the C19 methyl ether of aspercyclide A viagermyl-Stille macrocyclisation and ELISA evaluation of both enantiomers following optical resolution

J. L. Carr, J. J. P. Sejberg, F. Saab, M. D. Holdom, A. M. Davies, A. J. P. White, R. J. Leatherbarrow, A. J. Beavil, B. J. Sutton, S. D. Lindell and A. C. Spivey, Org. Biomol. Chem., 2011, 9, 6814
DOI: 10.1039/C1OB05862B

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