Braun reagent chiral synthesis

Fluvastatin (28, Scheme 2.4) is a member of the 3-hydroxy-3-methyl-glutaryl-coenzyme A (HMG CoA) reductase inhibitor family and is prescribed to treat hypercholesterolemia. As part of their nonracemic synthesis of fluvastatin, researchers at Novartis used a monoacetyltri-phenylglycol chiral auxiliary 25 originally reported by Braun and Devant. A diastereoselective lithium aldol reaction between Braun and Devant s reagent 25 and the fluarophenylindolenal 24 afforded the allylic alcohol 26 as... 

Several acetate containing chiral auxiliaries have been employed as reagents for asymmetric Aldol reactions in drug discovery programmes. Perhaps the most significant of these is Braun s reagent which has been used in the synthesis of hoth atorvastatin and fluvastatin. ... 

Atorvastatin, 217, a HMG-CoA inhibitor developed by Pfizer is a popular treatment for hypercholesterolemia. An early as)mimetric synthesis of the drug used an aldol reaction between the magnesium enolate of Braun s reagent 214 and aldehyde 213 to afford alcohol 215 in 97% ee and 60% yield (Scheme 14.75). Subsequent transesterification was used to remove the chiral auxiliary affording compound 216. 

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