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ChemInform Abstract

The synthesis of the interesting optically active bicyclic ketone (+)-( V) and its enantiomer (-)-(V) is described starting from (+)- norcamphor (+)-(I), derived from the commercially available (+)-endo norborneol. The usefulness of these synthons are shown by the stereocontrolled synthesis of (+)-juvabione (+)-(XV) in which the key step is the convex face selective 1,4-addition of a Grignard reagent leading to ketone (VII). is the key step. Via carbonyl transformation the enantiomer (-)-(V) is obtained, which in an identical approach as for (+)-(XV) gives the other title compound.