Date of Award

Spring 2015

Project Type


Program or Major


Degree Name

Doctor of Philosophy

First Advisor

Charles K Zercher

Second Advisor

Gary R Weisman

Third Advisor

Glen P Miller


A formal synthesis of the natural products CJ-12,954 and CJ-13,014 was successfully accomplished using the zinc-mediated tandem chain extension-aldol reaction methodology. This chemistry was performed on a chiral β-keto imide synthesized using a DCC coupling reaction. The diastereoselectivity of the aldol reaction was controlled by an Evans chiral auxiliary. Comparison between the reported and experimental spectral data for the spiroketals confirmed the structural assignment.

The diastereoselectivity of the homologation-cyclization-rearrangement-lactonization reaction of β-keto imide derived from phenyl carbamate-protected proline was studied. Tetra-n-butylammonium fluoride-mediated rearrangement of trimethylsilyl cyclopropanol demonstrated the role of chiral auxiliary and the amino acid stereocenter in controlling the diastereoselectivity of the bicyclic lactone formation.