121712-64-9Relevant academic research and scientific papers
Stereoselective reduction of β,δ-diketo esters. A novel strategy for the synthesis of artificial HMG-CoA reductase inhibitors
Hiyama,Reddy,Minami,Hanamoto
, p. 350 - 363 (2007/10/02)
Condensation of N-methoxy-N-methyl amides with the dianions of acetoacetates gives in good yields β,δ-diketo esters, which are reduced with Et2BOMe-NaBH4 in tetrahydrofuran-methanol highly selectively to give syn-β,δ-dihydroxy esters in one step. Similarly, the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer respectively are reduced to give syn-β,δ-dihydroxy esters of moderate enantiomeric excess. Higher diastereo- and enantioselectivity were achieved by reduction of the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer successively with diisobutylalane and with Et2BOMe-NaBH4. The resulting syn-diol esters were hydrolyzed and lactonized to give various types of β-hydroxy-δ-lactones commonly found in artificial HMG-CoA reductase inhibitors.
A FACILE ENTRY TO β,δ-DIKETO AND syn-β,δ-DIHYDROXY ESTERS
Hanamoto, Takeshi,Hiyama, Tamejiro
, p. 6467 - 6470 (2007/10/02)
Reaction of N-metoxy-N-methyl amides with the dianions of acetoacetates gives β,δ-diketo esters in yield of synthetic use, and the diketo esters were selectively reduced to syn-β,δ-dihydroxy esters, key intermediates of synthetic HMG-CoA reductase inhibit
