%0 Generic
%9 Doctoral Dissertation
%A Perez, Rachel
%D 2015
%F pittir:24699
%K Diversity-Oriented Synthesis, Marineosin A, spiroaminal, ruthenium-catalyzed enolate allylic alkylation, pyrrolidine scaffolds.
%T Efforts towards the Macrocyclic Core of Marineosin A and   Development of Pyrrolidine-Based Scaffolds for Diversity-Oriented Synthesis   
%U http://d-scholarship-dev.library.pitt.edu/24699/
%X The total synthesis of marineosin A, a unique spiroaminal with selective cytotoxicity, has been under investigation in our laboratory. A ruthenium-catalyzed enolate allylic alkylation methodology and azafulvene dimer-derived metathesis strategy have been considered as potential routes, towards the synthesis of the macrocyclic core of marineosin A.      A novel route to the synthesis of diverse pyrrolidine scaffolds, for diversity-oriented synthesis has additionally been under investigation in our laboratory.  The synthetic route encompasses a series of reductive amination, iodocyclization, azide substitution, and reductive deprotection to deliver the target diamine scaffolds in 14-16% yield. In addition, an asymmetric approach to the synthesis of (2S,3R,4R)-β–iodo amine has been presented, which takes advantage of selective Ru(II)-catalyzed Claisen rearrangement methodology.