Abstract
The synthesis of 6-tert-butyl-9-methoxy-14,15,17,18-tetramethyl[3.3]MPCP 11, via the TosMIC cyclo-condensation reaction followed by Wolff-Kishner reduction is described. Lewis acid (AlCl3-MeNO2) catalyzed reactions of 11 led only to de-tertbutylation and demethylation of the C(9)-methoxy group. A DFT analysis of the conformations of all of the synthesized [3.3]MPCPs products is also presented and a study of their Lewis acid-mediated properties. The contrast between the reactions of 11 with those of the corresponding [2.2]MPCPs is presented as is a DFT computational analysis of the various conformers of the molecules described herein.
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