Efforts towards the Macrocyclic Core of Marineosin A and Development of Pyrrolidine-Based Scaffolds for Diversity-Oriented Synthesis

Perez, Rachel (2015) Efforts towards the Macrocyclic Core of Marineosin A and Development of Pyrrolidine-Based Scaffolds for Diversity-Oriented Synthesis. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

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.

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Details

Item Type:	University of Pittsburgh ETD
Status:	Unpublished
Creators/Authors:	Creators Email Pitt Username ORCID Perez, Rachel rap52@pitt.edu RAP52
ETD Committee:	Title Member Email Address Pitt Username ORCID Committee Chair Nelson, Scott sgnelson@pitt.edu SGNELSON Committee Member Gold, Barry goldbi@pitt.edu GOLDBI Committee Member Horne, Seth horne@pitt.edu HORNE Committee Member Wilcox, Craig daylite@pitt.edu DAYLITE
Date:	27 September 2015
Date Type:	Publication
Defense Date:	13 May 2015
Approval Date:	27 September 2015
Submission Date:	9 April 2015
Access Restriction:	No restriction; Release the ETD for access worldwide immediately.
Number of Pages:	127
Institution:	University of Pittsburgh
Schools and Programs:	Dietrich School of Arts and Sciences > Chemistry
Degree:	PhD - Doctor of Philosophy
Thesis Type:	Doctoral Dissertation
Refereed:	Yes
Uncontrolled Keywords:	Diversity-Oriented Synthesis, Marineosin A, spiroaminal, ruthenium-catalyzed enolate allylic alkylation, pyrrolidine scaffolds.
Date Deposited:	28 Sep 2015 00:43
Last Modified:	15 Nov 2016 14:27
URI:	http://d-scholarship.pitt.edu/id/eprint/24699

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