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Issue 21, 2008
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Synthetic studies on the cornexistins: synthesis of (±)-5-epi-hydroxycornexistin

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Abstract

The synthesis of 5-epi-hydroxycornexistin (44), a diastereoisomer of the herbicidal natural product hydroxycornexistin (2) has been completed. Palladium mediated sp2–sp3 coupling of the stannane 25 and the chloride 31 and ring-closing metathesis of the resulting diene 32 has been used to construct the tricyclic lactone 34a, which possesses the nine-membered carbocyclic core found in the natural product, in good yield. The synthesis of 5-epi-hydroxycornexistin (44) has established the feasibility of using a furan as precursor for the cyclic anhydride unit present in the natural product and has demonstrated the viability of other late-stage transformations that will be used to prepare hydroxycornexistin (2).

Graphical abstract: Synthetic studies on the cornexistins: synthesis of (±)-5-epi-hydroxycornexistin

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Supplementary files

Article information


Submitted
02 Jul 2008
Accepted
31 Jul 2008
First published
08 Sep 2008

Org. Biomol. Chem., 2008,6, 4012-4025
Article type
Paper

Synthetic studies on the cornexistins: synthesis of (±)-5-epi-hydroxycornexistin

J. S. Clark, J. M. Northall, F. Marlin, B. Nay, C. Wilson, A. J. Blake and M. J. Waring, Org. Biomol. Chem., 2008, 6, 4012 DOI: 10.1039/B811245B

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