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

Clark, J.S. , Northall, J.M., Marlin, F., Nay, B., Wilson, C., Blake, A.J. and Waring, M.J. (2008) Synthetic studies on the cornexistins: synthesis of (+/-)-5-epi-hydroxycornexistin. Organic and Biomolecular Chemistry, 6(21), pp. 4012-4025. (doi: 10.1039/b811245b)

Abstract

The synthesis of 5-epi-hydroxycornexistin (44), a diastereoisomer of the herbicidal natural product hydroxycornexistin (2) has been completed. Palladium mediated sp(2)-sp(3) 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).

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Clark, Professor Stephen
• Authors: Clark, J.S., Northall, J.M., Marlin, F., Nay, B., Wilson, C., Blake, A.J., and Waring, M.J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic and Biomolecular Chemistry
• ISSN: 1477-0520