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Diastereoselective and enantioselective preparation of nor-mevaldic acid surrogates through desymmetrisation methodology. Enantioselective synthesis of (+) and (-) nor-mevalonic lactones

Botubol-Ares, J. M., Durán-Pena, M. J., Hernández-Galán, R., Collado, I. G., Harwood, L. M. and Macías-Sánchez, A. J. (2015) Diastereoselective and enantioselective preparation of nor-mevaldic acid surrogates through desymmetrisation methodology. Enantioselective synthesis of (+) and (-) nor-mevalonic lactones. Tetrahedron, 71 (40). pp. 7531-7538. ISSN 0040-4020

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To link to this item DOI: 10.1016/j.tet.2015.08.010

Abstract/Summary

Solvent-free desymmetrisation of a meso-dialdehyde with chiral alcohols, led to preparation of 4-silyloxy-6-alkyloxytetrahydro-2H-pyran-2-one derivatives with a 96% de. This methodology, which yields the corresponding methyl nor-mevaldates with 99% ee, has been applied to the enantioselective synthesis of the (-)-(R) and (+)-(S) nor-mevalonic acid lactones.

Item Type:Article
Refereed:Yes
Divisions:Interdisciplinary centres and themes > Chemical Analysis Facility (CAF)
Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:58197
Publisher:Elsevier

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