Total synthesis of (-)-halosaline by a ruthenium-catalyzed ring rearrangement

Article abstract of DOI:10.1016/S0040-4020(99)00299-9

The stereoselective synthesis of substituted piperidines by a ruthenium- catalyzed ring rearrangement of cyclopentene derivatives is demonstrated. The influence of different substituents and the effect of ethylene on the metathesis reaction is described. The ring rearrangement can be combined with a molybdenum-catalyzed cross metathesis reaction using allyltrimethyl silane as coupling partner. The first total synthesis of (-)-halosaline was accomplished via domino metathesis reaction utilizing Grubbs' ruthenium catalyst.