135972-31-5Relevant 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 novel enantioselective synthesis of HMG Co-A reductase inhibitor NK-104 and a related compound
Minami, Tatsuya,Hiyama, Tamejiro
, p. 7525 - 7526 (2007/10/02)
Optically active methyl 6-oxo-3,5-syn-isopropylidenedioxyhexanoate (5) was prepared by enantioselective syn-reduction of β,δ-diketo ester 2, followed by hydrolysis, protection of the diol moiety and ozonolysis, and was converted into a highly potent HMG Co-A reductase inhibitor NK-104 and an analogue.
