SHORT SYNTHESES OF (+ -)-TETRAPONERINES-5 AND (+/-)-TETRAPONERINES-6 - THE STRUCTURES OF TETRAPONERINES-1 AND TETRAPONERINES-2, AND A REVISION OF THE STRUCTURES OF (+)-TETRAPONERINES-5 AND (+)-TETRAPONERINES-6/

The structures and absolute configurations of (+)-tetraponerines-5 and -6 [(+)-T-5 and (+)-T-6], from the poison gland of the ant Tetraponer a sp., were reassigned as 7 and 8, respectively, on the basis of exten sive two-dimensional NMR and CD studies. These results led to structur e proposals 9 for T-1 and 10 for T-2, the two minor alkaloids of the v enom. The structures and relative configurations of T-5 and T-6 were s ubsequently confirmed by short stereoselective syntheses.