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. ORCID: https://orcid.org/0000-0002-8442-7380 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 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.