Transannular Cyclizations in the Pentacyclo(5.4.0.0(2,6).0(3,10)0(5,9)undecane-8,11-Dione System: A Reinvestigation

摘要

As part of an ongoing program that is involved with the synthesis and chemistry of polycyclic cage compounds, we have examined some interesting imine and ketone reductions in the pentacyclo (5.4.0.0 2,6.0 3,10.0 5,9) undecane ring system. These reductions result in the formation of heterocyclic hexacyclic cage systems via transannular cyclization reactions. Some of these reactions were studied previously by Sasaki and co-workers. As work progressed, we became aware of some discrepancies in spectral properties between compounds that we prepared and those that had been reported earlier. This led us to reexamine their earlier work in the light of our current findings. We now report the results of this reinvestigation. Keywords: Pentacycloundecanedione, Cage molecules, Reduction, Sodium borohydride, Lithium aluminum hydride, Sodium cyanoborohydride, Reprints. (MJM)