Chemoenzymatic access to enantiomeric bicyclo[2.2.1]heptan-2,5-diones.
A practical integrated process, combining an enzymatic resolution step with a few chemical transformations, is described for the synthesis of (1R, 4R)- and (2S, 4S)-bicyclo[2.2.1]heptan-2,5-diones 1 of high enantiomeric purity, starting from a standard mixture of (+/-)-endo- and exo-2-acetoxy-5-norbornene.
Weissfloch
A
A
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, Université René Descartes, Paris, France.
Azerad
R
R
D002175:Candida / Q000201:enzymology; D002236:Carbohydrate Conformation; D002849:Chromatography, Gas; D003460:Crystallization; D007202:Indicators and Reagents; D008049:Lipase; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009636:Norbornanes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification; D009904:Optical Rotation; D013237:Stereoisomerism
D007202:Indicators and Reagents; D009636:Norbornanes; C091064:2-acetoxy-5-norbornene; D008049:Lipase