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

Abstract

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 (þ)-(S) nor-mevalonic acid lactones.