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Novel Route to Functionalized Cyclooctanoids via [5+3] Cycloaddition

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posted on 2004-02-06, 00:00 authored by Urlam Murali Krishna, Kodand D. Deodhar, Girish K. Trivedi, Shaikh M. Mobin
The self-dimerization of 3-oxidopyrylium leading to stereocontrolled formation of highly functionalized cyclooctanoids is described. Different functionalities were introduced on the dimer (3) and the stereochemical outcome was determined by single-crystal X-ray analysis. It is noteworthy that the hydrogenation of 3 in ethanol solvent gave the transannulated product 5, whereas the expected dihydro product 4 was obtained when the reaction was run in nonnucleophilic solvents. The mechanistic pathway is discussed.