146579-00-2

Upstream product

• 719-80-2 Ethyl diphenylphosphinite 
• 1733-55-7 ethyl diphenylphosphinate 
• 118559-07-2 ethyl 3,3-bis(4-fluorophenyl)-3-hydroxy-2-(1-methylethyl)-propionate 
• 118559-09-4 2-di(4-fluorophenyl)methylene-3-methyl-1-butanol 
• 108-64-5 Ethyl isovalerate 

Downstream Products

• 146579-02-4 methyl (3S,5R,6E)-8-di(4-fluorophenyl)methylidene-3,5-isopropylidenedioxy-9-methyl-6-decenoate 

Relevant academic research and scientific papers

Synthesis of artificial HMG-CoA reductase inhibitors based on the olefination strategy

Synthetic methods were studied for optically active 6-oxo-3,5-isopropylidenedioxyhexanoate esters (4), which could be used as a key precursor of various kinds of artificial analogs of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors. An enantiomer (+)-4 was prepared by asymmetric reduction of β,δ-diketo esters derived from the Taber's alcohol or L-tartrate followed by a series of chemical transformations, and the desired enantiomer (-)-4 was prepared by the same asymmetric reduction starting from D-tartrate. The key intermediate (-)-4 was finally converted into a highly potent HMG-CoA reductase inhibitor, NK-104.

A novel enantioselective synthesis of HMG Co-A reductase inhibitor NK-104 and a related compound

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.