Asymmetric synthesis of 6-(2′,3′,4′,5′,6′-pentafluorophenyl)-δ-lactones via “allyl”boranes: application for the synthesis of fluorinated analog of key pharmacophore of statin drugs

Fluoroallylboration−Olefination for the Synthesis of (Z)-4,4-Difluoropent-2-enoates and 5,5-Difluoro-5,6-dihydropyran-2-ones

“…Sequential allylboration-ring-closing metathesis (RCM) is a demonstrated strategy for the preparation of α-pyrones, including 6-fluoroalkyl analogues . α-Pyrones are important constituents of natural products that have been exploited as end products or intermediates in synthetic and medicinal applications.…”

Ruthenium‐Catalyzed CC Coupling of Fluorinated Alcohols with Allenes: Dehydrogenation at the Energetic Limit of β‐Hydride Elimination

“…Herein, we report that certain fluorinated alcohols are capable of participating in redox-triggered carbonyl allylation, as illustrated by their regio-and diastereoselective ruthenium catalyzed CÀCc oupling to 1,1-disubstituted allenes to furnish adducts bearing all-carbon quaternary stereocenters. [10][11][12][13] Further, through as eries of experiments, including competition kinetics,w ed emonstrate that the alcohol dehydrogenation events in these processes occur near the energetic limit of b-hydride elimination.…”

A New and Efficient Synthesis of the HMG‐CoA Reductase Inhibitor Pitavastatin

“…Among other methods reported for the asymmetric synthesis of the side-chain moieties of statins were the application of a highly diastereoselective hetero-Diels -Alder reaction [10], of diastereoselective aldol reactions with (À)-(1S)-2-hydroxy-1,2,2-triphenylethyl acetate ((S)-HYTRA) [11], and of the Blaise reaction [12]. Finally, the synthesis of fluorinated analogues have recently been reported by Ramachandran and co-workers [13]. Pitavastatin is a powerful statin comprising a 3,5-dihydroxyhept-6-enoic acid substructure instead of the 3,5-dihydroxyheptanoic acid moiety [14] (Fig.…”