Chevalley, A., Prunet, J. , Mauduit, M. and Ferezou, J.-P. (2013) Model studies for a ring-closing metathesis approach to the Bafilomycin macrolactone core from a 2,2-dimethoxy tetraenic ester precursor. European Journal of Organic Chemistry, 2013(36), pp. 8265-8278. (doi: 10.1002/ejoc.201300559)
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Abstract
A ring-closing metathesis strategy is reported for the construction of the 16-membered macrolactone core of the bafilomycins. One decisive key feature is the presence of a 2,2-dimethoxyketal functionality at C-2 that provides the required flexibility to the tetraenic ester precursor, allowing the ring-closing metathesis reaction to take place. Three different model esters of increasing complexity were successfully subjected to the 1,3-diene-ene ring-closing metathesis reaction. The best promoter for the simplest esters was the Grubbs first-generation precatalyst. A Hoveyda–Grubbs-type trifluoromethylamido-containing precatalyst developed by Mauduit's group gave satisfactory results for the most complex ester. In all experiments, the 12-Z-configured isomer was obtained as the major product. Subsequent microwave-promoted methanol elimination was achieved on the simplest model compound using camphorsulfonic acid (CSA) as a catalyst. Under these conditions, a E to Z isomerization of the double bond at C-4, as well as ca. 50 % isomerization of the 12-Z double bond into the corresponding 12-E isomer, were observed.
Item Type: | Articles |
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Status: | Published |
Refereed: | Yes |
Glasgow Author(s) Enlighten ID: | Prunet, Dr Joelle |
Authors: | Chevalley, A., Prunet, J., Mauduit, M., and Ferezou, J.-P. |
College/School: | College of Science and Engineering > School of Chemistry |
Journal Name: | European Journal of Organic Chemistry |
Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA |
ISSN: | 1434-193X |
ISSN (Online): | 1099-0690 |
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