Diastereo- and enantio-selective synthesis of 6-heterosubstituted-3,5-dihydroxyesters: novel precursors of mevinolin analogues

Abstract

The diastereoselective addition of 1,3-bis(trimethylsilyloxy)-1-methoxybutadiene 2 to readily available α-heterosubstituted aldehydes (S)-1 affords after syn-diastereoselective reduction HMG-CoA-reductase inhibitor-precursors (S,R,S)-4 and 5 with various substitution patterns and high enantiomeric and diastereoisomeric excesses (ee = 93–>96%; de = 95–>96%) in good yields.