Abstract
AbstractA new synthetic method for the preparation of pitavastatin is described. The approach circumvents various synthetic problems associated with the buildup of the 3,5‐dihydroxy‐C7 acid side chain of HMG‐CoA reductase inhibitors (statins). The use of the C6‐amide derivative 5 instead of ester derivatives in the coupling reaction with carboxaldehyde 8 (Scheme 3) prevents undesired side reactions, such as eliminations and retro‐aldol reactions. The method provides synthetic statins, such as pitavastatin, in >99% ee and exceptionally high overall yield. The enantiomerically pure starting material, (3S)‐3‐{[(tert‐butyl)dimethylsilyl]oxy}‐5‐oxo‐5‐{[(1S)‐1‐phenylethyl]amino}pentanoic acid (3c), is prepared by an improved procedure from 3‐{[(tert‐butyl)dimethylsilyl]oxy}glutaric anhydride (1) and (1S)‐1‐phenylethylamine (2c; Scheme 1).
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