We
demonstrate a facile approach for the synthesis of gem-disubstituted cyclooctanoids, a motif found in several biologically
active compounds. Appropriately substituted 1-alkenyl-5-pentyn-1-ols
bearing gem-dialkyl substituents at either the C2,
C3, or C4 position serve as useful precursors to a number of cyclooct-4-enone
derivatives via a tandem, microwave-assisted oxyanionic 6-exo-dig cyclization/Claisen rearrangement
reaction. gem-Dialkyl activation is necessary for
these reactions to occur, as unactivated 1-alkenyl-5-pentyn-1-ols
fail to undergo 6-exo-dig cyclization
under the conditions employed. Further application of the methodology
to the corresponding gem-dialkoxy system was also
explored to facilitate access to more complex carbocycles.
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